Organo-catalyzed highly diastereo- and enantio-selective direct aldol reactions in water

被引：72
|
作者：
Zhao, Jun-Feng [1 ,2 ,3 ]
He, Long [4 ,5 ]
Jiang, Jun [1 ,2 ,3 ]
Tang, Zhuo [1 ,2 ,3 ]
Cun, Lin-Feng [1 ,2 ,3 ]
Gong, Liu-Zhu [1 ,2 ,3 ,4 ,5 ]
机构：
[1] Chinese Acad Sci, Key Lab Asymmetr Synthesis & Chirotechnol Sichuan, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Union Lab Asymmetr Synthesis, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
[4] Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[5] Dept Chem Sci & Technol China, Hefei 230026, Peoples R China
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 21期
基金：
中国国家自然科学基金;
关键词：
water; organocatalysis; direct aldol; diastereo- and enantio-selective;
D O I：
10.1016/j.tetlet.2008.03.131
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric direct aldol reactions of a wide scope of aromatic aldehydes, with unmodified ketones in the presence of 1 mol % of organocatalyst prepared from (2R,3R)-diethyl 2-amino-3-hydroxysuccinate and trans-4-hydroxy-L-proline, were performed in water, affording aldol products in high yields with excellent diastereoselectivities of up to >99:1 and enantioselectivities of up to 98%. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3372 / 3375
页数：4
相关论文
共 50 条
  • [1] Highly diastereo- and enantioselective direct aldol reactions in water
    Hayashi, Y
    Sumiya, T
    Takahashi, J
    Gotoh, H
    Urushima, T
    Shoji, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) : 958 - 961
  • [2] Highly diastereo- and enantio-selective epoxidation of secondary allylic alcohols catalyzed by styrene monooxygenase
    Lin, Hui
    Liu, Yan
    Wu, Zhong-Liu
    CHEMICAL COMMUNICATIONS, 2011, 47 (09) : 2610 - 2612
  • [3] Highly diastereo- and enantioselective direct aldol reactions of aldehydes and ketones catalyzed by siloxyproline in the presence of water
    Aratake, Seiji
    Itoh, Takahiko
    Okano, Tsubasa
    Nagae, Norio
    Sumiya, Tatsunobu
    Shoji, Mitsuru
    Hayashi, Yujiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (36) : 10246 - 10256
  • [4] Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes
    Cheng-Yu He
    Yun-Xuan Tan
    Xin Wang
    Rui Ding
    Yi-Fan Wang
    Feng Wang
    Dingding Gao
    Ping Tian
    Guo-Qiang Lin
    Nature Communications, 11
  • [5] Highly diastereo- and enantioselective direct aldol reaction in water
    Aratake, Seiji
    Okano, Tsubasa
    Itoh, Takahiko
    Sumiya, Tatsunobu
    Shoji, Mitsuru
    Hayashi, Yujiro
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [6] Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes
    He, Cheng-Yu
    Tan, Yun-Xuan
    Wang, Xin
    Ding, Rui
    Wang, Yi-Fan
    Wang, Feng
    Gao, Dingding
    Tian, Ping
    Lin, Guo-Qiang
    NATURE COMMUNICATIONS, 2020, 11 (01)
  • [7] Highly diastereo- and enantioselective Mukaiyama aldol reactions catalyzed by hydrogen bonding
    McGilvra, Jeff D.
    Unni, Aditya K.
    Modi, Kriti
    Rawal, Viresh H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (37) : 6130 - 6133
  • [8] Rhodium-catalysed diastereo- and enantio-selective cyclopropanation of α-boryl styrenes
    Sun, Xiao
    Gu, Peiming
    Qin, Jiao
    Su, Yan
    CHEMICAL COMMUNICATIONS, 2020, 56 (82) : 12379 - 12382
  • [9] Copper(I)/SaBOX catalyzed highly diastereo- and enantio-selective cyclopropanation of cis-1,2-disubstituted olefins with α-nitrodiazoacetates
    Feng, Liang-Wen
    Wang, Peng
    Wang, Lijia
    Tang, Yong
    SCIENCE BULLETIN, 2015, 60 (02) : 210 - 215
  • [10] Effect of counter-cations on aggregation and chiral discrimination: Application to highly diastereo- and enantio-selective syntheses
    Solladie-Cavallo, A
    ENANTIOMER, 1999, 4 (3-4): : 173 - 182
12345