A Modified and Highly Useful Protocol for the Bronsted Acid Catalyzed, Enantioselective, Vinylogous Mannich Reaction with Aliphatic Aldimines

被引：21
|
作者：
Abels, Falko [1 ]
Schneider, Christoph [1 ]
机构：
[1] Univ Leipzig, Inst Organ Chem, D-04103 Leipzig, Germany
来源：
SYNTHESIS-STUTTGART | 2011年 / 24期
关键词：
vinylogous Mannich reaction; phosphoric acid; organocatalyis; contact ion pair; dienolate; BINOL; EFFICIENT;
D O I：
10.1055/s-0031-1289303
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly enantioselective as well as diastereoselective catalytic vinylogous Mannich reactions have been accomplished for the first time with aliphatic straight-chain aldimines and O,O-silylketene acetals and furnish valuable synthetic building blocks in high enantiomeric purity.
引用
收藏
页码：4050 / 4058
页数：9
相关论文
共 50 条
  • [1] The Bronsted Acid Catalyzed, Enantioselective Vinylogous Mannich Reaction
    Sickert, Marcel
    Abels, Falko
    Lang, Matthias
    Sieler, Joachim
    Birkemeyer, Claudia
    Schneider, Christoph
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (09) : 2806 - 2818
  • [2] The enantioselective, Bronsted acid catalyzed, vinylogous Mannich reaction
    Sickert, Marcel
    Schneider, Christoph
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) : 3631 - 3634
  • [3] An enantioselective Bronsted acid catalyzed enamine Mannich reaction
    Tillman, A. Louise
    Dixon, Darren J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (04) : 606 - 609
  • [4] Bronsted acid-catalyzed, enantioselective, vinylogous Mannich reaction of vinylketene silyl N,O-acetals
    Giera, David S.
    Sickert, Marcel
    Schneider, Christoph
    ORGANIC LETTERS, 2008, 10 (19) : 4259 - 4262
  • [5] Development of the first Bronsted acid assisted enantioselective Bronsted acid catalyzed direct Mannich reaction
    Rueping, Magnus
    Sugiono, Erli
    Schoepke, Fenja R.
    SYNLETT, 2007, (09) : 1441 - 1445
  • [6] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [7] Highly Diastereo- and Enantioselective Vinylogous Mannich Reactions of Fluorinated Aldimines with Siloxyfurans
    Zhao, Qian-Yi
    Yuan, Zhi-Liang
    Shi, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (04) : 637 - 643
  • [8] Chiral bronsted acid catalyzed enantioselective Mannich-type reaction
    Yamanaka, Masahiro
    Itoh, Junji
    Fuchibe, Kohei
    Akiyama, Takahiko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) : 6756 - 6764
  • [9] A highly enantioselective Bronsted acid catalyzed reaction cascade
    Rueping, Magnus
    Antonchick, Andrey P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (31) : 5836 - 5838
  • [10] Chiral Bronsted Acid-Catalyzed Stereoselective Mannich-Type Reaction of Azlactones with Aldimines
    Avila, Eloah P.
    Justo, Rodrigo M. S.
    Goncalves, Vanessa P.
    Pereira, Adriane A.
    Diniz, Renata
    Amarante, Giovanni W.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 590 - 594
12345