Asymmetric Alkaloid Synthesis: A One-Pot Organocatalytic Reaction to Quinolizidine Derivatives

被引：162
作者：
Franzen, Johan [1 ]
Fisher, Andreas [1 ]
机构：
[1] Royal Inst Technol, Dept Chem, S-10044 Stockholm, Sweden
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 04期
基金：
瑞典研究理事会;
关键词：
acyliminium ion; alkaloids; asymmetric catalysis; cyclization; organocatalysis; IMINIUM ION CYCLIZATION; DOMINO MICHAEL-ALDOL; CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE SYNTHESIS; EPIMERIZATION; CATALYSIS; ENONES;
D O I：
10.1002/anie.200805130
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) One pot+two steps = three stereocenters: A short enantioselective synthesis to access the indolo[2,3a]quinolizidine and the benzo[a]quinolizidine skeleton has been developed (see scheme; TMS = trimethylsilyl, R1 = aromatic, R2 = 3-indoyl or 3,4-dimethoxyphenyl). The sequence involves an organocatalytic conjugate addition and subsequent acid-catalyzed cyclization of the acyliminium ion. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：787 / 791
页数：5
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