Asymmetric Cascade Assembly of 1,2-Diaza-1,3-dienes and α,β-Unsaturated Aldehydes via Dienamine Activation

被引：35
|
作者：
Ran, Guang-Yao [1 ]
Gong, Ming [2 ]
Yue, Jing-Fei [1 ]
Yang, Xing-Xing [1 ]
Zhou, Su-Lan [1 ]
Du, Wei [1 ]
Chen, Ying-Chun [1 ]
机构：
[1] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Chengdu 610041, Peoples R China
[2] Ruian City Peoples Hosp, Ruian 325200, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 07期
关键词：
ONE-POT SYNTHESIS; COPPER(I)-CATALYZED INTRAMOLECULAR AMINATION; DIPEPTIDYL-PEPTIDASE-IV; II RECEPTOR ANTAGONISTS; DIELS-ALDER REACTIONS; QUATERNARY STEREOCENTERS; PYRROLIZIDINE ALKALOIDS; NITROGEN-HETEROCYCLES; AZOMETHINE YLIDES; MICHAEL ADDITION;
D O I：
10.1021/acs.orglett.7b00636
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cascade vinylogous 1,6-Michael addition/1,4-proton shift/aza-Michael addition/hemiaminal formation sequence of 1,2-diaza-1,3-dienes and beta-substituted 2-butenals has been developed under the influence of dienamine activation of a chiral secondary amine. This method exhibits high regio- and chemoselectivity and provides an efficient and straightforward approach to bicyclic l,8-diazabicyclo[3.3.0]octane skeletons with a tetrasubstituted stereogenic center with fair to excellent enantioselectivity.
引用
收藏
页码：1874 / 1877
页数：4
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