Racemization processes at a quaternary carbon center in the context of the asymmetric Michael reaction

被引:17
|
作者
Tan, K
Alvarez, R
Nour, M
Cavé, C
Chiaroni, A
Riche, C
d'Angelo, J
机构
[1] Ctr Etud Pharmaceut, F-92296 Chatenay Malabry, France
[2] ICSN, CNRS, F-91198 Gif Sur Yvette, France
[3] UFR Pharm, Unite Mol Interet Biol, F-21079 Dijon, France
[4] Univ Vigo, Dept Quim Organ, Vigo 36200, Spain
关键词
asymmetric synthesis; Michael reaction; quaternary carbon center; racemization; X-ray crystallography;
D O I
10.1016/S0040-4039(01)00926-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several examples of racemization process at a quaternary carbon center affecting Michael adducts were reported. A brief statement to prevent the occurrence of the interfering retro-Michael reaction was also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5021 / 5023
页数:3
相关论文
共 50 条
  • [41] Organocatalytic asymmetric desymmetrization: efficient construction of spirocyclic oxindoles bearing a unique all-carbon quaternary stereogenic center via sulfa-Michael addition
    Yao, Lu
    Liu, Kang
    Tao, Hai-Yan
    Qiu, Guo-Fu
    Zhou, Xiang
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2013, 49 (54) : 6078 - 6080
  • [42] Effect of High Pressure on the Organocatalytic Asymmetric Michael Reaction: Highly Enantioselective Synthesis of γ-Nitroketones with Quaternary Stereogenic Centers
    Kwiatkowski, Piotr
    Dudzinski, Krzysztof
    Lyzwa, Dawid
    ORGANIC LETTERS, 2011, 13 (14) : 3624 - 3627
  • [43] ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS
    FUJI, K
    CHEMICAL REVIEWS, 1993, 93 (06) : 2037 - 2066
  • [44] Domino Michael-Michael and Aldol-Aldol Reactions: Diastereoselective Synthesis of Functionalized Cyclohexanone Derivatives Containing Quaternary Carbon Center
    Ghorai, Manas K.
    Halder, Sandipan
    Das, Subhomoy
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9700 - 9712
  • [45] Chiral Acid-Catalyzed Asymmetric Nazarov Reaction: Nucleophilic Construction of a Quaternary Asymmetric Center at the α-Position of the Keto Function
    Yaji, Kentaro
    Shindo, Mitsuru
    SYNLETT, 2009, (15) : 2524 - 2528
  • [46] Catalytic asymmetric intramolecular Michael reaction of aldehydes
    Fonseca, MTH
    List, B
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3958 - 3960
  • [47] Asymmetric Michael Reaction Catalyzed by Mimicked Peptides
    Bayat, Saadi
    Tejo, Bimo Ario
    Salleh, Abu Bakar
    Abdulmalek, Emilia
    Normi, Yahaya M.
    Rahman, Mohd Basyaruddin Abdul
    CATALYSIS LETTERS, 2014, 144 (02) : 222 - 228
  • [48] Organocatalytic asymmetric Michael reaction with acylsilane donors
    Wu, Lei
    Li, Guangxun
    Fu, Qingquan
    Yu, Luoting
    Tang, Zhuo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (03) : 443 - 447
  • [49] ULTRASOUND IRRADIATION EFFECTS ON THE ASYMMETRIC MICHAEL REACTION
    MIRZAAGHAYAN, M
    ETEMADMOGHADAM, G
    ZAPARUCHA, A
    BERLAN, J
    LOUPY, A
    KOENIG, M
    TETRAHEDRON-ASYMMETRY, 1995, 6 (11) : 2643 - 2646
  • [50] ASYMMETRIC INDUCTION IN A MICHAEL-TYPE REACTION
    LANGSTRO.B
    BERGSON, G
    ACTA CHEMICA SCANDINAVICA, 1973, 27 (08): : 3118 - 3119