- -

Synthesis of Functionalized Indoles with a Trifluoromethy-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with beta-Trifluoromethyl-alpha, beta-enones

RiuNet: Institutional repository of the Polithecnic University of Valencia

Share/Send to

Cited by

Statistics

Synthesis of Functionalized Indoles with a Trifluoromethy-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with beta-Trifluoromethyl-alpha, beta-enones

Show full item record

Blay, G.; Fernández, I.; Muñoz Roca, MDC.; Pedro, JR.; Vila, C. (2010). Synthesis of Functionalized Indoles with a Trifluoromethy-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with beta-Trifluoromethyl-alpha, beta-enones. Chemistry - A European Journal. 16(30):9117-9122. https://doi.org/10.1002/chem.201000568

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/150421

Files in this item

Item Metadata

Title: Synthesis of Functionalized Indoles with a Trifluoromethy-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with beta-Trifluoromethyl-alpha, beta-enones
Author: Blay, G. Fernández, I. Muñoz Roca, María Del Carmen Pedro, J. R. Vila, C.
UPV Unit: Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada
Issued date:
Abstract:
[EN] Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with beta-trifluoromethyl-alpha,beta-unsaturated ketones to give functionalized indoles ...[+]
Subjects: Alkylation , Aromatic substitution , Asymmetric catalysis , Enones , Fluorinated compounds
Copyrigths: Cerrado
Source:
Chemistry - A European Journal. (issn: 0947-6539 )
DOI: 10.1002/chem.201000568
Publisher:
John Wiley & Sons
Publisher version: https://doi.org/10.1002/chem.201000568
Project ID:
MINECO/CTQ2009-13083
MICINN/CTQ2006-14200
info:eu-repo/grantAgreement/Generalitat Valenciana//ACOMP%2F2009%2F338/ES/Diseño y síntesis de nuevos ligandos de tipo hidroxiamida y oxazolina derivados del ácido mandélico. Aplicación en reacciones catalíticas enantioselectivas de formación de enlaces carbono-carbono/
Thanks:
Financial support from the Ministerio de Ciencia e Innovacion and FEDER (grants CTQ2006-14199 and CTQ2009-13083) and from Generalitat Valenciana (ACOMP/2009/338) is acknowledged. CV. thanks the Generalitat Valenciana for ...[+]
Type: Artículo

References

Kirsch, P. (2004). Modern Fluoroorganic Chemistry. doi:10.1002/352760393x

Chambers, R. D. (2004). Fluorine in Organic Chemistry. doi:10.1002/9781444305371

Shah, P., & Westwell, A. D. (2007). The role of fluorine in medicinal chemistry. Journal of Enzyme Inhibition and Medicinal Chemistry, 22(5), 527-540. doi:10.1080/14756360701425014 [+]
Kirsch, P. (2004). Modern Fluoroorganic Chemistry. doi:10.1002/352760393x

Chambers, R. D. (2004). Fluorine in Organic Chemistry. doi:10.1002/9781444305371

Shah, P., & Westwell, A. D. (2007). The role of fluorine in medicinal chemistry. Journal of Enzyme Inhibition and Medicinal Chemistry, 22(5), 527-540. doi:10.1080/14756360701425014

Muller, K., Faeh, C., & Diederich, F. (2007). Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science, 317(5846), 1881-1886. doi:10.1126/science.1131943

Kirk, K. L. (2008). Fluorination in Medicinal Chemistry: Methods, Strategies, and Recent Developments. Organic Process Research & Development, 12(2), 305-321. doi:10.1021/op700134j

Purser, S., Moore, P. R., Swallow, S., & Gouverneur, V. (2008). Fluorine in medicinal chemistry. Chem. Soc. Rev., 37(2), 320-330. doi:10.1039/b610213c

Konno, T., Tanaka, T., Miyabe, T., Morigaki, A., & Ishihara, T. (2008). A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction. Tetrahedron Letters, 49(13), 2106-2110. doi:10.1016/j.tetlet.2008.01.122

Billard, T., & Langlois, B. R. (2007). How to Reach Stereogenic Trifluoromethylated Carbon? En Route to the «Grail» of the Asymmetric Trifluoromethylation Reaction. European Journal of Organic Chemistry, 2007(6), 891-897. doi:10.1002/ejoc.200600643

Shibata, N., Mizuta, S., & Kawai, H. (2008). Recent advances in enantioselective trifluoromethylation reactions. Tetrahedron: Asymmetry, 19(23), 2633-2644. doi:10.1016/j.tetasy.2008.11.011

Ma, J.-A., & Cahard, D. (2008). Update 1 of: Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions. Chemical Reviews, 108(9), PR1-PR43. doi:10.1021/cr800221v

Uneyama, K., Katagiri, T., & Amii, H. (2008). α-Trifluoromethylated Carbanion Synthons. Accounts of Chemical Research, 41(7), 817-829. doi:10.1021/ar7002573

Matsukawa, S., & Saijo, M. (2008). TTMPP-catalyzed trifluoromethylation of carbonyl compounds and imines with trifluoromethylsilane. Tetrahedron Letters, 49(31), 4655-4657. doi:10.1016/j.tetlet.2008.05.053

Zemtsov, A. A., Levin, V. V., Dilman, A. D., Struchkova, M. I., Belyakov, P. A., & Tartakovsky, V. A. (2009). Nucleophilic trifluoromethylation of arylidene Meldrum’s acids. Tetrahedron Letters, 50(25), 2998-3000. doi:10.1016/j.tetlet.2009.03.188

Dilman, A. D., Levin, V. V., Belyakov, P. A., Struchkova, M. I., & Tartakovsky, V. A. (2008). Nucleophilic trifluoromethylation of arylidenemalononitriles. Tetrahedron Letters, 49(28), 4352-4354. doi:10.1016/j.tetlet.2008.05.039

García Ruano, J. L., de Haro, T., Singh, R., & Cid, M. B. (2008). An Efficient Method for the Synthesis of Nitropiperidones. The Journal of Organic Chemistry, 73(3), 1150-1153. doi:10.1021/jo702130a

Powell, A., Al Nakeeb, M., Wilkinson, B., & Micklefield, J. (2007). Precursor-directed biosynthesis of nonribosomal lipopeptides with modified glutamate residues. Chemical Communications, (26), 2683. doi:10.1039/b706224a

Sosnovskikh, V. Y., Barabanov, M. A., & Usachev, B. I. (2004). A Novel Redox Reaction between 8-Aza-5,7-dimethyl-2-trifluoromethylchromone and Alkyl Mercaptoacetates. Facile Synthesis of CF3-Containing 2-Pyridone Derivatives. The Journal of Organic Chemistry, 69(24), 8297-8304. doi:10.1021/jo049117m

Miyake, N., & Kitazume, T. (2003). Microreactors for the synthesis of fluorinated materials. Journal of Fluorine Chemistry, 122(2), 243-246. doi:10.1016/s0022-1139(03)00109-x

Mancini, I., Guella, G., Zibrowius, H., & Pietra, F. (2003). On the origin of quasi-racemic aplysinopsin cycloadducts, (bis)indole alkaloids isolated from scleractinian corals of the family Dendrophylliidae. Involvement of enantiodefective Diels–Alderases or asymmetric induction in artifact processes involving adventitious catalysts? Tetrahedron, 59(44), 8757-8762. doi:10.1016/j.tet.2003.09.038

Kam, T.-S., & Choo, Y.-M. (2004). New Indole Alkaloids fromAlstonia macrophylla. Journal of Natural Products, 67(4), 547-552. doi:10.1021/np034041v

Kinsman, A. C., & Kerr, M. A. (2003). The Total Synthesis of (+)-Hapalindole Q by an Organomediated Diels−Alder Reaction. Journal of the American Chemical Society, 125(46), 14120-14125. doi:10.1021/ja036191y

Huber, U., Moore, R. E., & Patterson, G. M. L. (1998). Isolation of a Nitrile-Containing Indole Alkaloid from the Terrestrial Blue-Green AlgaHapalosiphondelicatulus. Journal of Natural Products, 61(10), 1304-1306. doi:10.1021/np9801561

Rawson, D. J., Dack, K. N., Dickinson, R. P., & James, K. (2002). The design and synthesis of a novel series of indole derived selective ETA antagonists. Bioorganic & Medicinal Chemistry Letters, 12(2), 125-128. doi:10.1016/s0960-894x(01)00660-6

Dillard, R. D., Bach, N. J., Draheim, S. E., Berry, D. R., Carlson, D. G., Chirgadze, N. Y., … Wery, J.-P. (1996). Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A2. 1. Indole-3-acetamides. Journal of Medicinal Chemistry, 39(26), 5119-5136. doi:10.1021/jm960485v

Chang-Fong, J., Rangisetty, J. B., Dukat, M., Setola, V., Raffay, T., Roth, B., & Glennon, R. A. (2004). 1,2,3,4-Tetrahydrocarbazoles as 5-HT6 serotonin receptor ligands. Bioorganic & Medicinal Chemistry Letters, 14(8), 1961-1964. doi:10.1016/j.bmcl.2004.01.071

Olah, G. A., Krishnamurti, R., & Prakash, G. K. S. (1991). Friedel–Crafts Alkylations. Comprehensive Organic Synthesis, 293-339. doi:10.1016/b978-0-08-052349-1.00065-2

Bandini, M., Melloni, A., & Umani-Ronchi, A. (2004). Neue katalytische Methoden in der stereoselektiven Friedel-Crafts-Alkylierung. Angewandte Chemie, 116(5), 560-566. doi:10.1002/ange.200301679

Bandini, M., Melloni, A., & Umani-Ronchi, A. (2004). New Catalytic Approaches in the Stereoselective Friedel–Crafts Alkylation Reaction. Angewandte Chemie International Edition, 43(5), 550-556. doi:10.1002/anie.200301679

Jørgensen, K. A. (2003). Asymmetric Friedel-CraftsReactions: Catalytic Enantioselective Addition of Aromatic and HeteroaromaticC-H Bonds to Activated Alkenes, Carbonyl Compounds, andImines. Synthesis, 2003(07), 1117-1125. doi:10.1055/s-2003-39176

Bandini, M., Umani-Ronchi, A., Melloni, A., & Tommasi, S. (2005). A Journey Across Recent Advances in Catalytic and Stereoselective Alkylation of Indoles. Synlett, 2005(08), 1199-1222. doi:10.1055/s-2005-865210

Poulsen, T. B., & Jørgensen, K. A. (2008). Catalytic Asymmetric Friedel−Crafts Alkylation ReactionsCopper Showed the Way. Chemical Reviews, 108(8), 2903-2915. doi:10.1021/cr078372e

Jensen, K. B., Thorhauge, J., Hazell, R. G., & Jørgensen, K. A. (2001). Catalytic Asymmetric Friedel–Crafts Alkylation ofβ,γ-Unsaturatedα-Ketoesters: Enantioselective Addition of Aromatic C−H Bonds to Alkenes. Angewandte Chemie, 113(1), 164-167. doi:10.1002/1521-3757(20010105)113:1<164::aid-ange164>3.0.co;2-v

Jensen, K. B., Thorhauge, J., Hazell, R. G., & Jørgensen, K. A. (2001). Catalytic Asymmetric Friedel-Crafts Alkylation of β,γ-Unsaturated α-Ketoesters: Enantioselective Addition of Aromatic C−H Bonds to Alkenes. Angewandte Chemie International Edition, 40(1), 160-163. doi:10.1002/1521-3773(20010105)40:1<160::aid-anie160>3.0.co;2-s

Evans, D. A., Scheidt, K. A., Fandrick, K. R., Lam, H. W., & Wu, J. (2003). Enantioselective Indole Friedel−Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes. Journal of the American Chemical Society, 125(36), 10780-10781. doi:10.1021/ja036985c

Zhuang, W., Hansen, T., & Jørgensen, K. A. (2001). Catalytic enantioselective alkylation of heteroaromatic compounds using alkylidene malonates. Chemical Communications, (4), 347-348. doi:10.1039/b009008p

Zhou, J., & Tang, Y. (2002). Sidearm Effect:  Improvement of the Enantiomeric Excess in the Asymmetric Michael Addition‡of Indoles to Alkylidene Malonates. Journal of the American Chemical Society, 124(31), 9030-9031. doi:10.1021/ja026936k

Zhou, J., & Tang, Y. (2004). Enantioselective Friedel–Crafts reaction of indoles with arylidene malonates catalyzed byiPr-bisoxazoline–Cu(OTf)2. Chem. Commun., (4), 432-433. doi:10.1039/b313197a

Zhou, J., Ye, M.-C., Huang, Z.-Z., & Tang, Y. (2004). Controllable Enantioselective Friedel−Crafts Reaction1between Indoles and Alkylidene Malonates Catalyzed by Pseudo-C3-Symmetric Trisoxazoline Copper(II) Complexes. The Journal of Organic Chemistry, 69(4), 1309-1320. doi:10.1021/jo035552p

Palomo, C., Oiarbide, M., Kardak, B. G., García, J. M., & Linden, A. (2005). Highly Enantioselective Friedel−Crafts Alkylations of Pyrroles and Indoles with α‘-Hydroxy Enones under Cu(II)-Simple Bis(oxazoline) Catalysis. Journal of the American Chemical Society, 127(12), 4154-4155. doi:10.1021/ja0423217

Evans, D. A., Fandrick, K. R., & Song, H.-J. (2005). Enantioselective Friedel−Crafts Alkylations of α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes. Journal of the American Chemical Society, 127(25), 8942-8943. doi:10.1021/ja052433d

Yang, H., Hong, Y.-T., & Kim, S. (2007). Catalytic Enantioselective Friedel−Crafts Alkylations of Indoles with α‘-Phosphoric Enones. Organic Letters, 9(12), 2281-2284. doi:10.1021/ol070548b

Desimoni, G., Faita, G., Toscanini, M., & Boiocchi, M. (2008). Asymmetric Friedel–Crafts Alkylation of Indoles with Methyl (E)-2-Oxo-4-aryl-3-butenoates Catalyzed by Sc(OTf)3/pybox. Chemistry - A European Journal, 14(12), 3630-3636. doi:10.1002/chem.200701908

Rueping, M., Nachtsheim, B. J., Moreth, S. A., & Bolte, M. (2008). Asymmetrische Brønsted-Säure-Katalyse: enantioselektive nucleophile Substitutionen und 1,4-Additionen. Angewandte Chemie, 120(3), 603-606. doi:10.1002/ange.200703668

Rueping, M., Nachtsheim, B. J., Moreth, S. A., & Bolte, M. (2008). Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4-Additions. Angewandte Chemie International Edition, 47(3), 593-596. doi:10.1002/anie.200703668

Singh, P. K., & Singh, V. K. (2008). Highly Enantioselective Friedel−Crafts Reaction of Indoles with 2-EnoylPyridine 1-Oxides Catalyzed by Chiral Pyridine 2,6-Bis(5′,5′-diphenyloxazoline)−Cu(II) Complexes†. Organic Letters, 10(18), 4121-4124. doi:10.1021/ol8016929

Boersma, A. J., Feringa, B. L., & Roelfes, G. (2009). Enantioselective Friedel-Crafts Reactions in Water Using a DNA-Based Catalyst. Angewandte Chemie, 121(18), 3396-3398. doi:10.1002/ange.200900371

Boersma, A. J., Feringa, B. L., & Roelfes, G. (2009). Enantioselective Friedel-Crafts Reactions in Water Using a DNA-Based Catalyst. Angewandte Chemie International Edition, 48(18), 3346-3348. doi:10.1002/anie.200900371

Liu, Y., Shang, D., Zhou, X., Liu, X., & Feng, X. (2009). Enantioselective Friedel-Crafts Alkylation of Indoles with Alkylidene Malonates Catalyzed byN,N′-Dioxide-Scandium(III) Complexes: Asymmetric Synthesis ofβ-Carbolines. Chemistry - A European Journal, 15(9), 2055-2058. doi:10.1002/chem.200802210

Zhuang, W., Hazell, R. G., & Jørgensen, K. A. (2005). Enantioselective Friedel–Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst – synthesis of optically active tetrahydro-β-carbolines. Organic & Biomolecular Chemistry, 3(14), 2566. doi:10.1039/b505220c

Herrera, R. P., Sgarzani, V., Bernardi, L., & Ricci, A. (2005). Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes by Using a Simple Thiourea Organocatalyst. Angewandte Chemie, 117(40), 6734-6737. doi:10.1002/ange.200500227

Herrera, R. P., Sgarzani, V., Bernardi, L., & Ricci, A. (2005). Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes by Using a Simple Thiourea Organocatalyst. Angewandte Chemie International Edition, 44(40), 6576-6579. doi:10.1002/anie.200500227

Jia, Y.-X., Zhu, S.-F., Yang, Y., & Zhou, Q.-L. (2006). Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes. The Journal of Organic Chemistry, 71(1), 75-80. doi:10.1021/jo0516537

Itoh, J., Fuchibe, K., & Akiyama, T. (2008). Chiral Phosphoric Acid Catalyzed Enantioselective Friedel–Crafts Alkylation of Indoles with Nitroalkenes: Cooperative Effect of 3 Å Molecular Sieves. Angewandte Chemie, 120(21), 4080-4082. doi:10.1002/ange.200800770

Itoh, J., Fuchibe, K., & Akiyama, T. (2008). Chiral Phosphoric Acid Catalyzed Enantioselective Friedelâ Crafts Alkylation of Indoles with Nitroalkenes: Cooperative Effect of 3â Ã Molecular Sieves. Angewandte Chemie International Edition, 47(21), 4016-4018. doi:10.1002/anie.200800770

Ganesh, M., & Seidel, D. (2008). Catalytic Enantioselective Additions of Indoles to Nitroalkenes. Journal of the American Chemical Society, 130(49), 16464-16465. doi:10.1021/ja8063292

Arai, T., & Yokoyama, N. (2008). Tandem Catalytic Asymmetric Friedel-Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters. Angewandte Chemie, 120(27), 5067-5070. doi:10.1002/ange.200801373

Arai, T., & Yokoyama, N. (2008). Tandem Catalytic Asymmetric Friedel-Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters. Angewandte Chemie International Edition, 47(27), 4989-4992. doi:10.1002/anie.200801373

Paras, N. A., & MacMillan, D. W. C. (2002). The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes. Journal of the American Chemical Society, 124(27), 7894-7895. doi:10.1021/ja025981p

Bandini, M., Fagioli, M., Garavelli, M., Melloni, A., Trigari, V., & Umani-Ronchi, A. (2004). Can Simple Enones Be Useful Partners for the Catalytic Stereoselective Alkylation of Indoles? The Journal of Organic Chemistry, 69(22), 7511-7518. doi:10.1021/jo0487202

Terada, M., & Sorimachi, K. (2007). Enantioselective Friedel−Crafts Reaction of Electron-Rich Alkenes Catalyzed by Chiral Brønsted Acid. Journal of the American Chemical Society, 129(2), 292-293. doi:10.1021/ja0678166

Bartoli, G., Bosco, M., Carlone, A., Pesciaioli, F., Sambri, L., & Melchiorre, P. (2007). Organocatalytic Asymmetric Friedel−Crafts Alkylation of Indoles with Simple α,β-Unsaturated Ketones. Organic Letters, 9(7), 1403-1405. doi:10.1021/ol070309o

Chen, W., Du, W., Yue, L., Li, R., Wu, Y., Ding, L.-S., & Chen, Y.-C. (2007). Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones. Org. Biomol. Chem., 5(5), 816-821. doi:10.1039/b616504d

Blay, G., Fernández, I., Pedro, J. R., & Vila, C. (2007). Highly Enantioselective Friedel−Crafts Alkylations of Indoles with Simple Enones Catalyzed by Zirconium(IV)−BINOL Complexes†. Organic Letters, 9(13), 2601-2604. doi:10.1021/ol0710820

Blay, G., Fernández, I., Monleón, A., Muñoz, M. C., Pedro, J. R., & Vila, C. (2009). Synthesis of Functionalized Indoles with an α-Stereogenic Ketone Moiety Through an Enantioselective Friedel-Crafts Alkylation with (E)-1,4-Diaryl-2-butene-1,4-diones. Advanced Synthesis & Catalysis, 351(14-15), 2433-2440. doi:10.1002/adsc.200900357

Chi, Y., Scroggins, S. T., & Fréchet, J. M. J. (2008). One-Pot Multi-Component Asymmetric Cascade Reactions Catalyzed by Soluble Star Polymers with Highly Branched Non-Interpenetrating Catalytic Cores. Journal of the American Chemical Society, 130(20), 6322-6323. doi:10.1021/ja8013456

Hong, L., Wang, L., Chen, C., Zhang, B., & Wang, R. (2009). An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes. Advanced Synthesis & Catalysis, 351(5), 772-778. doi:10.1002/adsc.200800710

Galzerano, P., Pesciaioli, F., Mazzanti, A., Bartoli, G., & Melchiorre, P. (2009). Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes. Angewandte Chemie, 121(42), 8032-8034. doi:10.1002/ange.200903803

Galzerano, P., Pesciaioli, F., Mazzanti, A., Bartoli, G., & Melchiorre, P. (2009). Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes. Angewandte Chemie International Edition, 48(42), 7892-7894. doi:10.1002/anie.200903803

Cai, Q., Zhao, Z.-A., & You, S.-L. (2009). Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis. Angewandte Chemie, 121(40), 7564-7567. doi:10.1002/ange.200903462

Cai, Q., Zhao, Z.-A., & You, S.-L. (2009). Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis. Angewandte Chemie International Edition, 48(40), 7428-7431. doi:10.1002/anie.200903462

Adachi, S., Tanaka, F., Watanabe, K., & Harada, T. (2009). Oxazaborolidinone-Catalyzed Enantioselective Friedel−Crafts Alkylation of Furans and Indoles with α,β-Unsaturated Ketones. Organic Letters, 11(22), 5206-5209. doi:10.1021/ol9021436

Huang, Y., Tokunaga, E., Suzuki, S., Shiro, M., & Shibata, N. (2010). Enantioselective Friedel−Crafts Reaction of β-Trifluoromethylated Acrylates with Pyrroles and Its Application to the Synthesis of Trifluorinated Heliotridane. Organic Letters, 12(5), 1136-1138. doi:10.1021/ol100171z

Sasaki, S., Yamauchi, T., & Higashiyama, K. (2010). Dy(OTf)3/Pybox-catalyzed enantioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones. Tetrahedron Letters, 51(17), 2326-2328. doi:10.1016/j.tetlet.2010.02.121

Funabiki, K., Matsunaga, K., Nojiri, M., Hashimoto, W., Yamamoto, H., Shibata, K., & Matsui, M. (2003). The Use of Trifluoroacetaldehyde Ethyl Hemiacetal or Hydrate in a Simple and Practical Regioselective Synthesis of β-Hydroxy-β-trifluoromethyl Ketones from Enamines and Imines. The Journal of Organic Chemistry, 68(7), 2853-2860. doi:10.1021/jo026697j

Funabiki, K., Nagaya, H., Ishihara, M., & Matsui, M. (2006). Direct aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with ketones by use of the combination of amines and acids. Tetrahedron, 62(21), 5049-5053. doi:10.1016/j.tet.2006.03.053

3 ae www.ccdc.cam. ac.uk/data_request/cif

Blond, G., Billard, T., & Langlois, B. R. (2001). Reactivity of Stable Trifluoroacetaldehyde Hemiaminals. 1. An Unexpected Reaction with Enolizable Carbonyl Compounds. The Journal of Organic Chemistry, 66(14), 4826-4830. doi:10.1021/jo015587u

[-]

recommendations

 

This item appears in the following Collection(s)

Show full item record