- -

Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes

Mostrar el registro completo del ítem

Blay, G.; Cardona, L.; Fernández, I.; Marco-Aleixandre, A.; Muñoz Roca, MDC.; Pedro, JR. (2009). Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes. Organic & Biomolecular Chemistry. 7(20):4301-4308. https://doi.org/10.1039/b911592g

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/150442

Ficheros en el ítem

Metadatos del ítem

Título: Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes
Autor: Blay, G. Cardona, L. Fernández, I. Marco-Aleixandre, A. Muñoz Roca, María Del Carmen Pedro, J. R.
Entidad UPV: Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada
Fecha difusión:
Resumen:
[EN] A mandelamide ligand, derived from (S)-mandelic acid and (S)-phenylethanamine, catalyzes the addition of aryl-, alkyl-and silyl-alkynylzinc reagents to aromatic and heteroaromatic aldehydes with good yields and good ...[+]
Derechos de uso: Cerrado
Fuente:
Organic & Biomolecular Chemistry. (issn: 1477-0520 )
DOI: 10.1039/b911592g
Editorial:
The Royal Society of Chemistry
Versión del editor: https://doi.org/10.1039/b911592g
Código del Proyecto:
info:eu-repo/grantAgreement/MEC//CTQ2006-14199/ES/DISEÑO Y SINTESIS DE NUEVOS LIGANDOS DE TIPO HIDROXIAMIDA Y OXAZOLINA DERIVADOS DEL ACIDO MANDELICO. APLICACION EN REACCIONES CATALITICAS ENANTIOSELECTIVAS DE FORMACION DE ENLACES CARBONO-CARBONO/
Agradecimientos:
Financial support from the Ministerio de Ciencia e Innovacion and FEDER (CTQ 2006-14199/BQU) is gratefully acknowledged.
Tipo: Artículo

References

Trost, B. M., & Weiss, A. H. (2009). The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups. Advanced Synthesis & Catalysis, 351(7-8), 963-983. doi:10.1002/adsc.200800776

Pu, L. (2003). Asymmetric alkynylzinc additions to aldehydes and ketones. Tetrahedron, 59(50), 9873-9886. doi:10.1016/j.tet.2003.10.042

Cozzi, P. G., Hilgraf, R., & Zimmermann, N. (2004). Acetylenes in Catalysis: Enantioselective Additions to Carbonyl Groups and Imines and Applications Beyond. European Journal of Organic Chemistry, 2004(20), 4095-4105. doi:10.1002/ejoc.200400246 [+]
Trost, B. M., & Weiss, A. H. (2009). The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups. Advanced Synthesis & Catalysis, 351(7-8), 963-983. doi:10.1002/adsc.200800776

Pu, L. (2003). Asymmetric alkynylzinc additions to aldehydes and ketones. Tetrahedron, 59(50), 9873-9886. doi:10.1016/j.tet.2003.10.042

Cozzi, P. G., Hilgraf, R., & Zimmermann, N. (2004). Acetylenes in Catalysis: Enantioselective Additions to Carbonyl Groups and Imines and Applications Beyond. European Journal of Organic Chemistry, 2004(20), 4095-4105. doi:10.1002/ejoc.200400246

Armstrong, A., & Emmerson, D. P. G. (2009). Enantioselective Synthesis of Allenamides via Sulfimide [2,3]-Sigmatropic Rearrangement. Organic Letters, 11(7), 1547-1550. doi:10.1021/ol900146s

Boone, M. A., McDonald, F. E., Lichter, J., Lutz, S., Cao, R., & Hardcastle, K. I. (2009). 1,5-α-d-Mannoseptanosides, Ring-Size Isomers That Are Impervious to α-Mannosidase-Catalyzed Hydrolysis. Organic Letters, 11(4), 851-854. doi:10.1021/ol8028065

Chandrasekhar, S., Vijaykumar, B. V. D., & Pratap, T. V. (2008). Total synthesis of (−)-lentiginosine. Tetrahedron: Asymmetry, 19(6), 746-750. doi:10.1016/j.tetasy.2008.02.017

Hayashi, Y., Yamaguchi, H., Toyoshima, M., Okado, K., Toyo, T., & Shoji, M. (2008). Formal Total Synthesis of Fostriecin via 1,4-Asymmetric Induction Using Cobalt-Alkyne Complex. Organic Letters, 10(7), 1405-1408. doi:10.1021/ol800195g

Li, J., Park, S., Miller, R. L., & Lee, D. (2009). Tandem Enyne Metathesis−Metallotropic [1,3]-Shift for a Concise Total Syntheses of (+)-Asperpentyn, (−)-Harveynone, and (−)-Tricholomenyn A. Organic Letters, 11(3), 571-574. doi:10.1021/ol802675j

Nagamitsu, T., Takano, D., Seki, M., Arima, S., Ohtawa, M., Shiomi, K., … Ōmura, S. (2008). The total synthesis and biological evaluation of nafuredin-γ and its analogues. Tetrahedron, 64(35), 8117-8127. doi:10.1016/j.tet.2008.06.066

Roethle, P. A., & Trauner, D. (2006). Expedient Synthesis of (±)-Bipinnatin J. Organic Letters, 8(2), 345-347. doi:10.1021/ol052922i

Trost, B. M., Mueller, T. J. J., & Martinez, J. (1995). Ruthenium Catalyzed Synthesis of Butenolides and Pentenolides via Contra-Electronic .alpha.-Alkylation of Hydroxyalkynoates. Journal of the American Chemical Society, 117(7), 1888-1899. doi:10.1021/ja00112a004

Frantz, D. E., Fässler, R., & Carreira, E. M. (2000). Facile Enantioselective Synthesis of Propargylic Alcohols by Direct Addition of Terminal Alkynes to Aldehydes. Journal of the American Chemical Society, 122(8), 1806-1807. doi:10.1021/ja993838z

Anand, N. K., & Carreira, E. M. (2001). A Simple, Mild, Catalytic, Enantioselective Addition of Terminal Acetylenes to Aldehydes. Journal of the American Chemical Society, 123(39), 9687-9688. doi:10.1021/ja016378u

Boyall, D., Frantz, D. E., & Carreira, E. M. (2002). Efficient Enantioselective Additions of Terminal Alkynes and Aldehydes under Operationally Convenient Conditions. Organic Letters, 4(15), 2605-2606. doi:10.1021/ol026282k

Boyall, D., López, F., Sasaki, H., Frantz, D., & Carreira, E. M. (2000). Enantioselective Addition of 2-Methyl-3-butyn-2-ol to Aldehydes:  Preparation of 3-Hydroxy-1-butynes. Organic Letters, 2(26), 4233-4236. doi:10.1021/ol006791r

El-Sayed, E., Anand, N. K., & Carreira, E. M. (2001). Asymmetric Synthesis of γ-Hydroxy α,β-Unsaturated Aldehydes via Enantioselective Direct Addition of Propargyl Acetate to Aldehydes. Organic Letters, 3(19), 3017-3020. doi:10.1021/ol016431j

Zhong, J.-C., Hou, S.-C., Bian, Q.-H., Yin, M.-M., Na, R.-S., Zheng, B., … Wang, M. (2009). Highly Enantioselective Zinc/Amino Alcohol-Catalyzed Alkynylation of Aldehydes. Chemistry - A European Journal, 15(13), 3069-3071. doi:10.1002/chem.200900070

Xu, Z., Wu, N., Ding, Z., Wang, T., Mao, J., & Zhang, Y. (2009). l-Proline-derived tertiary amino alcohol as a new chiral ligand for enantioselective alkynylation of aldehydes. Tetrahedron Letters, 50(8), 926-929. doi:10.1016/j.tetlet.2008.12.030

Xu, Z., Mao, J., & Zhang, Y. (2008). Unmodified chiral primary amino alcohol as a new ligand for enantioselective alkynylation of aldehydes. Catalysis Communications, 10(1), 113-117. doi:10.1016/j.catcom.2008.08.006

Emmerson, D. P. G., Hems, W. P., & Davis, B. G. (2006). Carbohydrate-Derived Amino-Alcohol Ligands for Asymmetric Alkynylation of Aldehydes. Organic Letters, 8(2), 207-210. doi:10.1021/ol052503l

Watts, C. C., Thoniyot, P., Hirayama, L. C., Romano, T., & Singaram, B. (2005). Enantioselective alkynylations of aromatic and aliphatic aldehydes catalyzed by terpene derived chiral amino alcohols. Tetrahedron: Asymmetry, 16(10), 1829-1835. doi:10.1016/j.tetasy.2005.03.036

Yamashita, M., Yamada, K., & Tomioka, K. (2005). Catalytic Asymmetric Addition of Terminal Alkynes to Aldehydes Mediated by (1R,2R)-2-(Dimethylamino)- 1,2-diphenylethanol. Advanced Synthesis & Catalysis, 347(11-13), 1649-1652. doi:10.1002/adsc.200505157

Trost, B. M., Weiss, A. H., & Jacobi von Wangelin, A. (2006). Dinuclear Zn-Catalyzed Asymmetric Alkynylation of Unsaturated Aldehydes. Journal of the American Chemical Society, 128(1), 8-9. doi:10.1021/ja054871q

Jiang, B., Chen, Z., & Xiong, W. (2002). Highly enantioselective alkynylation of aldehydes catalyzed by a readily available chiral amino alcohol-based ligand. Chemical Communications, (14), 1524-1525. doi:10.1039/b203984b

Jiang, B., & Feng, Y. (2002). Enantioselective alkynylation of a prochiral ketone catalyzed by C2-symmetric diamino diols. Tetrahedron Letters, 43(16), 2975-2977. doi:10.1016/s0040-4039(02)00444-6

Omote, M., Eto, Y., Tarui, A., Sato, K., & Ando, A. (2009). Enantioselective alkynylation of aldehydes with chiral β-imino α-perfluoroalkylpropanol derivatives. Tetrahedron: Asymmetry, 20(5), 602-604. doi:10.1016/j.tetasy.2009.02.047

Li, M., Zhu, X.-Z., Yuan, K., Cao, B.-X., & Hou, X.-L. (2004). Highly enantioselective phenylacetylene addition to aldehydes catalyzed by a chiral N,O-ferrocene ligand. Tetrahedron: Asymmetry, 15(2), 219-222. doi:10.1016/j.tetasy.2003.12.002

Dahmen, S. (2004). Enantioselective Alkynylation of Aldehydes Catalyzed by [2.2]Paracyclophane-Based Ligands. Organic Letters, 6(13), 2113-2116. doi:10.1021/ol049596b

Xu, Z., Mao, J., & Zhang, Y. (2008). Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine–titanium complex. Organic & Biomolecular Chemistry, 6(7), 1288. doi:10.1039/b719624e

Kang, Y., Wang, R., Liu, L., Da, C., Yan, W., & Xu, Z. (2005). Enantioselective alkynylation of aromatic aldehydes catalyzed by new chiral oxazolidine ligands. Tetrahedron Letters, 46(5), 863-865. doi:10.1016/j.tetlet.2004.11.165

Braga, A. L., Appelt, H. R., Silveira, C. C., Wessjohann, L. A., & Schneider, P. H. (2002). Facile and practical enantioselective synthesis of propargylic alcohols by direct addition of alkynes to aldehydes catalyzed by chiral disulfide–oxazolidine ligands. Tetrahedron, 58(52), 10413-10416. doi:10.1016/s0040-4020(02)01420-5

Xu, Z., Wang, R., Xu, J., Da, C., Yan, W., & Chen, C. (2003). Highly Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by aβ-Sulfonamide Alcohol–Titanium Complex. Angewandte Chemie International Edition, 42(46), 5747-5749. doi:10.1002/anie.200352572

Xu, Z., Chen, C., Xu, J., Miao, M., Yan, W., & Wang, R. (2004). Highly Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by a Camphorsulfonamide Ligand. Organic Letters, 6(8), 1193-1195. doi:10.1021/ol036418u

Ni, M., Wang, R., Han, Z., Mao, B., Da, C., Liu, L., & Chen, C. (2005). Synthesis of NewC2-Symmetrical Bissulfonamide Ligands and Application in the Enantioselective Addition of Alkynylzinc to Aldehydes and Ketones. Advanced Synthesis & Catalysis, 347(11-13), 1659-1665. doi:10.1002/adsc.200505162

Xu, Z., Lin, L., Xu, J., Yan, W., & Wang, R. (2006). Asymmetric Addition of Phenylacetylene to Aldehydes Catalyzed by β-Sulfonamide Alcohol-Titanium Complex. Advanced Synthesis & Catalysis, 348(4-5), 506-514. doi:10.1002/adsc.200505453

Forrat, V. J., Prieto, O., Ramón, D. J., & Yus, M. (2006). trans-1-Sulfonylamino-2-isoborneolsulfonylaminocyclohexane Derivatives: Excellent Chiral Ligands for the Catalytic Enantioselective Addition of Organozinc Reagents to Ketones. Chemistry - A European Journal, 12(16), 4431-4445. doi:10.1002/chem.200501397

Qiu, L., Wang, Q., Lin, L., Liu, X., Jiang, X., Zhao, Q., … Wang, R. (2009). Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral β-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system. Chirality, 21(2), 316-323. doi:10.1002/chir.20583

Li, Y.-M., Tang, Y.-Q., Hui, X.-P., Huang, L.-N., & Xu, P.-F. (2009). Synthesis of new β-hydroxy amide ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aliphatic and vinyl aldehydes. Tetrahedron, 65(18), 3611-3614. doi:10.1016/j.tet.2009.03.005

Fang, T., Du, D.-M., Lu, S.-F., & Xu, J. (2005). Synthesis ofC3-Symmetric Tris(β-hydroxy amide) Ligands and Their Ti(IV) Complex-Catalyzed Enantioselective Alkynylation of Aldehydes. Organic Letters, 7(11), 2081-2084. doi:10.1021/ol050047v

Li, X., Lu, G., Jia, X., Wu, Y., & Chan, A. S. C. (2007). Highly enantioselective alkynylation of aldehydes using a new BINOL/Ti(OiPr)4/chiral sulfonamide catalyst system. Chirality, 19(8), 638-641. doi:10.1002/chir.20433

Lu, G., Li, X., Chan, W. L., & Chan, A. S. C. (2002). Titanium-catalyzed enantioselective alkynylation of aldehydes. Chemical Communications, (2), 172-173. doi:10.1039/b107817h

Lu, G., Li, X., Chen, G., Chan, W. L., & Chan, A. S. . (2003). Effective activation of chiral BINOL/Ti(OiPr)4 catalyst with phenolic additives for the enantioselective alkynylation of aldehydes. Tetrahedron: Asymmetry, 14(4), 449-452. doi:10.1016/s0957-4166(03)00021-1

Ruan, J., Lu, G., Xu, L., Li, Y.-M., & Chan, A. S. C. (2008). Catalytic Asymmetric Alkynylation and Arylation of Aldehydes by an H8-Binaphthyl-Based Amino Alcohol Ligand. Advanced Synthesis & Catalysis, 350(1), 76-84. doi:10.1002/adsc.200700215

Gao, G., Moore, D., Xie, R.-G., & Pu, L. (2002). Highly Enantioselective Phenylacetylene Additions to Both Aliphatic and Aromatic Aldehydes. Organic Letters, 4(23), 4143-4146. doi:10.1021/ol026921r

Gao, G., Xie, R.-G., & Pu, L. (2004). Asymmetric Catalysis Special Feature Part I: Highly enantioselective alkyne additions to aldehydes in the presence of 1,1’-bi-2-naphthol and hexamethylphosphoramide. Proceedings of the National Academy of Sciences, 101(15), 5417-5420. doi:10.1073/pnas.0307136101

Xu, M.-H., & Pu, L. (2002). A New 1,1‘-Binaphthyl-Based Catalyst for the Enantioselective Phenylacetylene Addition to Aromatic Aldehydes without Using a Titanium Complex. Organic Letters, 4(25), 4555-4557. doi:10.1021/ol027110q

Moore, D., & Pu, L. (2002). BINOL-Catalyzed Highly Enantioselective Terminal Alkyne Additions to Aromatic Aldehydes. Organic Letters, 4(11), 1855-1857. doi:10.1021/ol025825n

Moore, D., Huang, W.-S., Xu, M.-H., & Pu, L. (2002). Greatly enhanced enantioselectivity by an apparently remote steric effect in the 1,1′-binaphthyl-catalyzed alkynylzinc addition to aldehydes. Tetrahedron Letters, 43(49), 8831-8834. doi:10.1016/s0040-4039(02)02211-6

Li, Z.-B., & Pu, L. (2004). BINOL−Salen-Catalyzed Highly Enantioselective Alkyne Additions to Aromatic Aldehydes. Organic Letters, 6(6), 1065-1068. doi:10.1021/ol0498139

Gao, G., Wang, Q., Yu, X.-Q., Xie, R.-G., & Pu, L. (2006). Highly Enantioselective Synthesis of γ-Hydroxy-α,β-acetylenic Esters by Asymmetric Alkyne Addition to Aldehydes. Angewandte Chemie International Edition, 45(1), 122-125. doi:10.1002/anie.200500469

Yang, F., Xi, P., Yang, L., Lan, J., Xie, R., & You, J. (2007). Facile, Mild, and Highly Enantioselective Alkynylzinc Addition to Aromatic Aldehydes by BINOL/N-Methylimidazole Dual Catalysis. The Journal of Organic Chemistry, 72(14), 5457-5460. doi:10.1021/jo0707535

Takita, R., Yakura, K., Ohshima, T., & Shibasaki, M. (2005). Asymmetric Alkynylation of Aldehydes Catalyzed by an In(III)/BINOL Complex. Journal of the American Chemical Society, 127(40), 13760-13761. doi:10.1021/ja053946n

Blay, G., Fernández, I., Marco-Aleixandre, A., & Pedro, J. R. (2005). Chiral bis(amino alcohol)oxalamides as ligands for asymmetric catalysis. Ti(IV) catalyzed enantioselective addition of diethylzinc to aldehydes. Tetrahedron: Asymmetry, 16(6), 1207-1213. doi:10.1016/j.tetasy.2005.01.039

Blay, G., Fernández, I., Hernández-Olmos, V., Marco-Aleixandre, A., & Pedro, J. R. (2007). Tailoring the ligand structure to the reagent in the mandelamide-Ti(IV) catalyzed enantioselective addition of dimethyl- and diethylzinc to aldehydes. Journal of Molecular Catalysis A: Chemical, 276(1-2), 235-243. doi:10.1016/j.molcata.2007.07.019

Blay, G., Fernández, I., Hernández-Olmos, V., Marco-Aleixandre, A., & Pedro, J. R. (2005). Enantioselective addition of dimethylzinc to aldehydes catalyzed by N-substituted mandelamide-Ti(IV) complexes. Tetrahedron: Asymmetry, 16(11), 1953-1958. doi:10.1016/j.tetasy.2005.04.011

Blay, G., Fernández, I., Marco-Aleixandre, A., & Pedro, J. R. (2006). Catalytic Asymmetric Addition of Dimethylzinc to α-Ketoesters, Using Mandelamides as Ligands. Organic Letters, 8(7), 1287-1290. doi:10.1021/ol052997m

Blay, G., Fernández, I., Marco-Aleixandre, A., & Pedro, J. R. (2006). Mandelamide−Zinc-Catalyzed Enantioselective Alkyne Addition to Heteroaromatic Aldehydes#. The Journal of Organic Chemistry, 71(17), 6674-6677. doi:10.1021/jo0610255

Njardarson, J. T., Gaul, C., Shan, D., Huang, X.-Y., & Danishefsky, S. J. (2004). Discovery of Potent Cell Migration Inhibitors through Total Synthesis:  Lessons from Structure−Activity Studies of (+)-Migrastatin. Journal of the American Chemical Society, 126(4), 1038-1040. doi:10.1021/ja039714a

Ishizaki, M., & Hoshino, O. (1994). Efficient ligands, chiral 2-[2,2-dimethyl-1-(2-pyridyl)propoxy]-1,1-diarylethanols for highly enantioselective addition of alkynylzinc reagents to various aldehydes. Tetrahedron: Asymmetry, 5(10), 1901-1904. doi:10.1016/s0957-4166(00)86262-x

[-]

recommendations

 

Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro completo del ítem