α,β-Unsaturated Acyl Cyanides as New Bis-Electrophiles for Enantioselective Organocatalyzed Formal [3+3]Spiroannulation

被引：46
作者：
Goudedranche, Sebastien [1 ]
Bugaut, Xavier [1 ]
Constantieux, Thierry [1 ]
Bonne, Damien [1 ]
Rodriguez, Jean [1 ]
机构：
[1] Aix Marseille Univ, Cent Marseille, CNRS, UMR iSm2 7313, F-13397 Marseille, France
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 02期
关键词：
domino reactions; enantioselectivity; glutarimides; organocatalysis; spiroannulation; ASYMMETRIC CONJUGATE ADDITION; MICHAEL ADDITION; ABSOLUTE-CONFIGURATION; LEWIS-ACID; EFFICIENT SYNTHESIS; CONSTRUCTION; ALKALOIDS; DERIVATIVES; ALDEHYDES; CYCLIZATION;
D O I：
10.1002/chem.201303613
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
alpha, beta-Unsaturated acyl cyanides are key bis-electrophile substrates for successful domino enantioselective organocatalyzed Michael-intramolecular acylation domino sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4,5] decanone ring systems by a formal [3+ 3] spiroannulation, constituting a rare example of synthesis of glutarimides in an optically active form.
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收藏
页码：410 / 415
页数：6
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