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

作者：Guang‐Yao Ran, Ming Gong, Jing‐Fei Yue, Xing‐Xing Yang, Su-Lan Zhou, Wei Du, Ying‐Chun Chen · 发表于：Organic Letters · 年份：2017 · DOI：10.1021/acs.orglett.7b00636 · 被引用次数：43 · 研究领域：Asymmetric Synthesis and Catalysis、Cyclopropane Reaction Mechanisms、Synthetic Organic Chemistry Methods

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 β-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.