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
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 30期
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
  • [21] Organocatalyzed Asymmetric Michael Reaction in Ionic Liquids-Carbon Dioxide
    Rosa, Joao N.
    Afonso, Carlos A. M.
    IONIC LIQUIDS IN ORGANIC SYNTHESIS, 2007, 950 : 235 - 245
  • [22] Organocatalytic Asymmetric Synthesis of Pentasubstituted Tetrahydrothiopyrans Bearing a Quaternary Centre through a Double Michael Reaction
    Mondal, Buddhadeb
    Pan, Subhas Chandra
    SYNLETT, 2018, 29 (05) : 576 - 580
  • [23] Asymmetric Michael reaction of malonate derivatives with α,β-unsaturated ketones using chiral quaternary ammonium salts
    Cho, Min Je
    Cho, Myoung Gi
    Huh, Sun Chul
    Kim, Sung Min
    Lee, Kilsung
    Koh, Kwang Oh
    Mang, Joo Yang
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2006, 27 (06) : 857 - 862
  • [24] METHYL-METHACRYLATE AS ACCEPTOR IN THE ASYMMETRIC MICHAEL REACTION USING CHIRAL BETA-ENAMINOESTERS - SIMULTANEOUS, COMPLETE STEREOCONTROL OF A QUATERNARY CARBON CENTER AND A TERTIARY ONE IN THE BETA-POSITION
    CAVE, C
    DALEY, V
    DANGELO, J
    GUINGANT, A
    TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 79 - 82
  • [25] Electronic control of chiral quaternary center creation in the intramolecular asymmetric Heck reaction
    Busacca, CA
    Grossbach, D
    Campbell, SJ
    Dong, Y
    Eriksson, MC
    Harris, RE
    Jones, PJ
    Kim, JY
    Lorenz, JC
    McKellop, KB
    O'Brien, EM
    Qiu, FG
    Simpson, RD
    Smith, L
    So, RC
    Spinelli, EM
    Vitous, J
    Zavattaro, C
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16): : 5187 - 5195
  • [26] Asymmetric Organocatalytic Synthesis of β-Hydroxyynones with a Quaternary Carbon Center under Aqueous Conditions
    Kang, Guowei
    Jiang, Jun
    Liu, Hongxin
    Wu, Huayue
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (01) : 5 - S26
  • [27] A New Powerful Strategy for the Organocatalytic Asymmetric Construction of a Quaternary Carbon Stereogenic Center
    Inokoishi, Yogo
    Sasakura, Niiha
    Nakano, Keiji
    Ichikawa, Yoshiyasu
    Kotsuki, Hiyoshizo
    ORGANIC LETTERS, 2010, 12 (07) : 1616 - 1619
  • [28] Diphenylprolinol Silyl Ether Catalyzed Asymmetric Michael Reaction of Nitroalkanes and β, β-Disubstituted α, β-Unsaturated Aldehydes for the Construction of All-Carbon Quaternary Stereogenic Centers
    Hayashi, Yujiro
    Kawamoto, Yuya
    Honda, Masaki
    Okamura, Daichi
    Umemiya, Shigenobu
    Noguchi, Yuka
    Mukaiyama, Takasuke
    Sato, Itaru
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (38) : 12072 - 12082
  • [29] Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
    Hayashi, Yujiro
    ORGANIC SYNTHESES, 2022, 99 : 68 - 78
  • [30] Microwave-assisted Tertiary Carbon Radical Reaction for Construction of Quaternary Carbon Center
    Sato, Ryota
    Okamoto, Ryuji
    Ishizuka, Takumi
    Nakayama, Atsushi
    Karanjit, Sangita
    Namba, Kosuke
    CHEMISTRY LETTERS, 2019, 48 (05) : 414 - 417
12345