New β-amino thiols as efficient catalysts for highly enantioselective alkenylzinc addition to aldehydes

被引：33
|
作者：
Tseng, SL [1 ]
Yang, TK [1 ]
机构：
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan
来源：
TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 04期
关键词：
D O I：
10.1016/j.tetasy.2004.11.093
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A series of new optically active beta-amino thiols and thiolacetates prepared from the simple natural amino acid, (S)-(-)-valine, were found to be effective catalysts for the enantioselective addition of alkenylzinc to alclehydes and thereby providing an efficient route for chiral (E)-allylic alcohols with ees of up to >99% in the presence of 7a (1 mol %). (C) 2005 Published by Elsevier Ltd.
引用
收藏
页码：773 / 782
页数：10
相关论文
共 50 条
  • [1] Aziridine-modified amino alcohols as efficient modular catalysts for highly enantioselective alkenylzinc additions to aldehydes
    Braga, Antonio L.
    Paixao, Marcio W.
    Westermann, Bernhard
    Schneider, Paulo H.
    Wessjohann, Ludger A.
    SYNLETT, 2007, (06) : 917 - 920
  • [2] The application of chiral amino thiols as catalysts in the enantioselective addition of diethylzinc to aldehydes
    Tseng, SL
    Yang, TK
    TETRAHEDRON-ASYMMETRY, 2004, 15 (21) : 3375 - 3380
  • [3] New chiral catalysts for the highly enantioselective addition of diethylzinc to aldehydes
    Jin, MJ
    Ahn, SJ
    Lee, KS
    TETRAHEDRON LETTERS, 1996, 37 (48) : 8767 - 8770
  • [4] New class of amino-phosphinite chiral catalysts for the highly enantioselective addition of arylzinc reagents to aldehydes
    Godoi, Marcelo
    Alberto, Eduardo E.
    Paixao, Marcio W.
    Soares, Liliana A.
    Schneider, Paulo H.
    Braga, Antonio L.
    TETRAHEDRON, 2010, 66 (06) : 1341 - 1345
  • [5] Enantioselective addition of alkenylzinc reagents to aldehydes with organoboronates as the alkenyl source
    Chai, Zhuo
    Liu, Xin-Yuan
    Zhang, Jun-Kang
    Zhao, Gang
    TETRAHEDRON-ASYMMETRY, 2007, 18 (06) : 724 - 728
  • [6] FERROCENYLSELENO AMINO-ALCOHOLS AS NEW CATALYSTS FOR THE HIGHLY ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES
    FUKUZAWA, S
    TSUDZUKI, K
    TETRAHEDRON-ASYMMETRY, 1995, 6 (05) : 1039 - 1042
  • [7] ENANTIOSELECTIVE ADDITION OF (Z)-ALKENYLZINC AND (E)-ALKENYLZINC BROMIDES TO ALDEHYDES - ASYMMETRIC-SYNTHESIS OF SEC-ALLYLALCOHOLS
    OPPOLZER, W
    RADINOV, RN
    TETRAHEDRON LETTERS, 1991, 32 (41) : 5777 - 5780
  • [8] Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes
    Marigo, M
    Schulte, T
    Franzén, J
    Jorgensen, KA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) : 15710 - 15711
  • [9] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes
    Braga, AL
    Paixao, MW
    LUdtke, DS
    Silveira, CC
    Rodrigues, OED
    ORGANIC LETTERS, 2003, 5 (15) : 2635 - 2638
  • [10] New polymer anchored chiral amino oxazolines as effective catalysts for enantioselective addition of diethylzinc to aldehydes
    Shaikh, NS
    Deshpande, VH
    Bedekar, AV
    TETRAHEDRON LETTERS, 2002, 43 (32) : 5587 - 5589
12345