A Systematic Study of Chiral Homoprolinols and Their Derivatives in the Catalysis of Enantioselective Addition of Diethylzinc to Aldehydes

被引：9
作者：
Liu, Chang-Lu [1 ,2 ]
Wei, Chang-Yong [1 ]
Wang, Shi-Wen [1 ]
Peng, Yun-Gui [1 ]
机构：
[1] Southwest Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China
[2] Sichuan Univ Arts & Sci, Dept Chem & Chem Engn, Dazhou 635000, Peoples R China
来源：
CHIRALITY | 2011年 / 23卷 / 10期
关键词：
gamma-amino alcohol; homoprolinol; enantioselective addition; diethylzinc; ASYMMETRIC ORGANOZINC ADDITIONS; AMINO-ALCOHOLS; GAMMA-AMINO; BETA-AMINO; LIGANDS; BENZALDEHYDE; DIALKYLZINCS; AMINOALCOHOLS; ALKYLATION; REAGENTS;
D O I：
10.1002/chir.21017
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Homoprolinol analogs, a class of optically active gamma-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these gamma-amino alcohols with those by the beta-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the gamma-amino alcohols are superior to the corresponding beta-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient gamma-amino alcohol catalysts based on pyrrolidine framework. Chirality 23:921-928, 2011. (C) 2011 Wiley-Liss, Inc.
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收藏
页码：921 / 928
页数：8
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共 84 条
  • [1] Chiral amide from (1S,2R)-(+)-norephedrine alkaloid in the enantioselective addition of diethylzinc to aryl and heteroaryl aldehydes
    Ananthi, Nallamuthu
    Balakrishnan, Umesh
    Vinu, Ajayan
    Ariga, Katsuhiko
    Velmathi, Sivan
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (15) : 1731 - 1735
  • [2] Enantioselective addition of diethylzinc to benzaldehyde catalysed by chiral, bridged resorcinarenes: a stereoselectivity model based on chirality transfer
    Arnott, G
    Hunter, R
    [J]. TETRAHEDRON, 2006, 62 (05) : 992 - 1000
  • [3] α-hydroxy carboxylic acids:: new ligands for diethylzinc additions to aldehydes
    Bauer, T
    Tarasiuk, J
    [J]. TETRAHEDRON LETTERS, 2002, 43 (04) : 687 - 689
  • [4] Enantioselective diethylzinc addition to aldehydes catalyzed by Ti(IV) complex of unsymmetrical chiral bis(sulfonamide) ligands of trans-cyclohexane 1,2-diamine
    Bisai, Alakesh
    Singh, Pradeep K.
    Singh, Vinod K.
    [J]. TETRAHEDRON, 2007, 63 (03) : 598 - 601
  • [5] Kinetic aspects of nonlinear effects in asymmetric catalysis
    Blackmond, DG
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 402 - 411
  • [6] Synthesis of chiral pentacyclo-undecane ligands and their use in the enantioselective alkylation of benzaldehyde with diethylzinc
    Boyle, GA
    Govender, T
    Kruger, HG
    Maguire, GEM
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (17) : 2661 - 2666
  • [7] Synthesis of new chiral imidazolidine disulfides derived from L-cystine and their application in the enantioselective addition of diethylzinc to aldehydes
    Braga, AL
    Vargas, F
    Silveira, CC
    de Andrade, LH
    [J]. TETRAHEDRON LETTERS, 2002, 43 (13) : 2335 - 2337
  • [8] Efficient chirality switching in the addition of diethylzinc to aldehydes in the presence of simple chiral α-amino amides
    Burguete, M. Isabel
    Collado, Manuel
    Escorihuela, Jorge
    Luis, Santiago V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) : 9002 - 9005
  • [9] Substrate dependence of nonlinear effects: Mechanistic probe and practical applications
    Chen, YK
    Costa, AM
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) : 5378 - 5379
  • [10] Chiral ligand 2-(2′-piperidinyl)pyridine:: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes
    Cheng, Yan-Qin
    Bian, Zheng
    Kang, Chuan-Qing
    Guo, Hai-Quan
    Gao, Lian-Xun
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (13) : 1572 - 1575
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