Catalytic Asymmetric Construction of Spiro(γ-butyrolactam-γ-butyrolactone) Moieties through Sequential Reactions of Cyclic Imino Esters with Morita-Baylis-Hillman Bromides

被引：47
作者：
Teng, Huai-Long [1 ]
Huang, He [1 ]
Wang, Chun-Jiang [1 ,2 ]
机构：
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 40期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; bromides; diastereoselectivity; enantioselectivity; imino esters; spiro compounds; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; CONJUGATE ADDITION-ELIMINATION; ACTIVATED ALLYLIC ACETATES; AZOMETHINE YLIDES; 3+2 ANNULATION; MICROBIAL METABOLITE; EFFICIENT SYNTHESIS; ACID DERIVATIVES; FACILE SYNTHESIS; QUATERNARY;
D O I：
10.1002/chem.201201475
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：12614 / 12618
页数：5
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