Citation: Zhang Xiong, Feng Kaixiang, Xia Aibao. Asymmetric Organocatalytic Construction of Functionalized Bicyclic Lactams[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3373-3380. doi: 10.6023/cjoc201806010 shu

Asymmetric Organocatalytic Construction of Functionalized Bicyclic Lactams

a.
School of Science & Technology, Zhejiang International Studies University, Hangzhou 310023
b.
Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalyti3 Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Zhang Xiong, xiongzhang1212@126.com Xia Aibao, xiaaibao@zjut.edu.cn
Received Date: 7 June 2018
Revised Date: 20 August 2018
Available Online: 5 December 2018
Fund Project: Project supported by the Natural Science Foundation of Zhejiang Province (No. LY18B020017)the Natural Science Foundation of Zhejiang Province LY18B020017

Figures(2)

A novel enantioselective organocatalytic cascade Michael-hemiaminalization-hemiacetalization reaction of α, β-unsaturated aldehydes with α-ketoamides as binucleophiles has been developed. A series of chiral functionalized bicyclic lactams with two cis contiguous stereogenic centers have been synthesized in up to 97% yield with up to >20:1 dr and up to >99% ee.
- asymmetric synthesis,
- Michael-hemiaminalization-hemiacetalization reaction,
- bicyclic lactam
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