Enantioselective Formal [3+3] Cycloadditions of Ketones and Cyclic 1-Azadienes by Cascade Enamine-Enamine Catalysis

被引：47
作者：
He, Xiao-Long [1 ]
Xiao, You-Cai [1 ]
Du, Wei [1 ]
Chen, Ying-Chun [1 ,2 ]
机构：
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, West China Sch Pharm, Chengdu 610041, Peoples R China
[2] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 08期
关键词：
3+3] cycloaddition; aminocatalysis; cascade catalysis; enantioselectivity; regioselectivity; DIELS-ALDER REACTIONS; DIPHENYLPROLINOL SILYL ETHER; ALPHA; BETA-UNSATURATED ALDEHYDES; ASYMMETRIC-SYNTHESIS; AZOMETHINE IMINES; MICHAEL ADDITION; METHYL KETONES; ALDOL REACTION; ANNULATION; CONSTRUCTION;
D O I：
10.1002/chem.201404550
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An asymmetric formal [3+3] cycloaddition process with diversely structured aliphatic ketones and electron-deficient cyclic 1-azadienes was developed by cascade enamine-enamine catalysis of a cinchona-based primary amine. This sequence involved a domino Michael addition-Mannich reaction to afford spirocyclic architectures in excellent diastereo- and enantioselectivity. Importantly, high regioselectivity was realized for a number of unsymmetrical aliphatic ketone substrates.
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收藏
页码：3443 / 3448
页数：6
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