Catalytic asymmetric carbonyl-ene reactions with alkynylogous and vinylogous glyoxylates: Application to controlled synthesis of chiral isocarbacyclin analogues

被引:34
|
作者
Mikami, K
Yoshida, A
Matsumoto, Y
机构
[1] Department of Chemical Technology, Tokyo Institute of Technology, Tokyo 152, Meguro-ku
关键词
D O I
10.1016/0040-4039(96)01954-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric carbonyl-ene reaction with alkynylogous and vinylogous glyoxylates (1, 2) catalyzed by a binaphthol-derived chiral titanium complex is described. The catalytic asymmetric ene reaction with aldehyde (I) can be applied to the double asymmetric synthesis of isocarbacyclin analogues bearing a 2-allenyl side chain. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:8515 / 8518
页数:4
相关论文
共 21 条
  • [1] CATALYTIC ASYMMETRIC CARBONYL-ENE REACTIONS
    BERRISFORD, DJ
    BOLM, C
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16): : 1717 - 1719
  • [2] Asymmetric Carbonyl-ene Reactions Promoted by Chiral Catalysts
    Zhang Yongli
    Zhang Rui
    Chang Honghong
    Wei Wenlong
    Li Xing
    PROGRESS IN CHEMISTRY, 2014, 26 (09) : 1492 - 1505
  • [3] DOUBLE ASYMMETRIC-SYNTHESIS BY ASYMMETRIC CATALYTIC CARBONYL-ENE TYPE REACTION WITH CHIRAL ENE COMPONENTS - ASYMMETRIC CATALYTIC SYNTHESIS OF ASPARTYL DIPEPTIDE SWEETENER
    TERADA, M
    SAYO, N
    MIKAMI, K
    SYNLETT, 1995, (05) : 411 - 415
  • [4] Asymmetric catalysis of carbonyl-ene and aldol reactions with fluoral by chiral binaphthol-derived titanium complex
    Mikami, K
    Yajima, T
    Takasaki, T
    Matsukawa, S
    Terada, M
    Uchimaru, T
    Maruta, M
    TETRAHEDRON, 1996, 52 (01) : 85 - 98
  • [5] ASYMMETRIC ADDITION-REACTION TO NON-PROCHIRAL CARBONYL COMPOUND - ASYMMETRIC CATALYTIC FORMALDEHYDE-ENE REACTION FOR ISOCARBACYCLIN SYNTHESIS
    MIKAMI, K
    YOSHIDA, A
    SYNLETT, 1995, (01) : 29 - 31
  • [6] Application of catalytic asymmetric reactions to the synthesis of chiral pesticides
    Zhang, WH
    Yang, CL
    Wang, MH
    Jiang, F
    Jiang, MG
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (08) : 741 - 749
  • [7] Palladium(II) Complexes of C2-Bridged Chiral Diphosphines: Application to Enantioselective Carbonyl-Ene Reactions
    Luo, He-Kuan
    Woo, Yuan-Ling
    Schumann, Herbert
    Jacob, Chacko
    van Meurs, Martin
    Yang, Hai-Yan
    Tan, Yen-Ting
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) : 1356 - 1364
  • [8] C2-symmetric copper(II) complexes as chiral Lewis acids.: Catalytic enantioselective carbonyl-ene reactions with glyoxylate and pyruvate esters
    Evans, DA
    Tregay, SW
    Burgey, CS
    Paras, NA
    Vojkovsky, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) : 7936 - 7943
  • [9] Asymmetric Calcium Catalysis: Highly Enantioselective Carbonyl-Ene and Friedel-Crafts Reactions for the Synthesis of Quaternary a-Hydroxy Esters Bearing a Trifluoromethyl Group
    Rueping, Magnus
    Bootwicha, Teerawut
    Kambutong, Supakeat
    Sugiono, Erli
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (06) : 1195 - 1198
  • [10] Modular chiral bidentate phosphonites: Design, synthesis, and application in catalytic asymmetric hydroformylation reactions
    Zhao, Baoguo
    Peng, Xingao
    Wang, Zheng
    Xia, Chungu
    Ding, Kuiling
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (26) : 7847 - 7857