THE ASYMMETRIC MICHAEL REACTION INVOLVING CHIRAL IMINES - USE OF ACRYLONITRILE AS ACCEPTOR AND SUBSEQUENT FUNCTIONALIZATION OF THE ADDUCTS

被引:8
|
作者
DESMAELE, D
ZOUHIRI, F
DANGELO, J
机构
[1] Laboratoire de Chimie Organique associé au CNRS, Centre d'Etudes Pharmaceutiques, 92296 Châtenay-Malabry
关键词
ASYMMETRIC MICHAEL ADDITION; CHIRAL IMINES; WITTIG REACTION; EPOXY-SILANES; TRIAZOLE FORMATION;
D O I
10.1016/0957-4166(94)80071-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Condensation of chiral imines 1 and acrylonitrile led to adduct (R)-6 with an ee greater than or equal to 95 %. This adduct has then been converted into chiral synthons 9, 11, 12 and 17.
引用
收藏
页码:1645 / 1648
页数:4
相关论文
共 50 条
  • [41] Asymmetric aza-Diels-Alder reaction of Danishefsky's diene with imines in a chiral reaction medium
    Pegot, Bruce
    Van Buu, Olivier Nguyen
    Gori, Didier
    Vo-Thanh, Giang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2
  • [42] Asymmetric Diels-Alder Reaction Involving Chiral Benzimidazoles as Organocatalysts
    Mirgane, Nitin A.
    Karnik, Anil V.
    CHIRALITY, 2011, 23 (05) : 404 - 407
  • [43] Asymmetric Michael reaction promoted by new chiral phase-transfer catalysts
    Arai, S
    Tokumaru, K
    Aoyama, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (05) : 646 - 648
  • [44] The first example of asymmetric Michael reaction catalyzed by chiral alkali metal alkoxides
    Belokon, YN
    Kochetkov, KA
    Churkina, TD
    Chesnokov, AA
    Smirnov, VV
    Ikonnikov, NS
    Orlova, SA
    RUSSIAN CHEMICAL BULLETIN, 1998, 47 (01) : 74 - 81
  • [45] Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (II)
    Fan, Huidan
    Zhang, Conghai
    Yan, Shengjiao
    Lin, Jun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (01) : 160 - 164
  • [46] NEW-TYPE OF ASYMMETRIC DOUBLE MICHAEL REACTION INDUCED BY CHIRAL ACETAL
    KATO, K
    SUEMUNE, H
    SAKAI, K
    TETRAHEDRON LETTERS, 1993, 34 (31) : 4979 - 4980
  • [47] The first example of asymmetric Michael reaction catalyzed by chiral alkali metal alkoxides
    Yu. N. Belokon'
    K. A. Kochetkov
    T. D. Churkina
    A. A. Chesnokov
    V. V. Smirnov
    N. S. Ikonnikov
    S. A. Orlova
    Russian Chemical Bulletin, 1998, 47 : 74 - 81
  • [48] Natural Sugars Derived Chiral Ionic Liquids for Asymmetric Michael Addition Reaction
    Jayachandra, R.
    Reddy, Sabbasani Rajasekhara
    Balakrishna
    CHEMISTRYSELECT, 2016, 1 (10): : 2341 - 2353
  • [49] ASYMMETRIC MICHAEL REACTION VIA CHIRAL ALPHA,BETA-UNSATURATED ALDIMINES
    HASHIMOTO, SI
    KOMESHIMA, N
    YAMADA, SI
    KOGA, K
    TETRAHEDRON LETTERS, 1977, (33) : 2907 - 2908
  • [50] Asymmetric Michael addition reaction using a chiral catalyst containing amino diol
    Prabagaran, N
    Abraham, S
    Sundararajan, G
    ARKIVOC, 2002, : 212 - 226