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Organocatalytic Asymmetric Domino Oxa-Michael-Mannich-[1,3]-Amino Rearrangement Reaction of N-Tosylsalicylimines to α,β-Unsaturated Aldehydes by Diarylprolinol Silyl Ethers

Sha Hu, Jiaqi Wang, Guanxin Huang, Kejie Zhu and Fener Chen*

*Department of Chemistry, Fudan University, Shanghai 200433, China, Email:

S. Hu, J. Wang, G. Huang, K. Zhu, F. Chen, J. Org. Chem., 2020, 85, 4011-4018.

DOI: 10.1021/acs.joc.9b02939


Diarylprolinol silyl ether catalyzes an asymmetric enantioselective domino oxa-Michael-Mannich-[1,3]-amino rearrangement reaction of N-tosylsalicylimines with a wide range of α,β-unsaturated aldehydes to produce the corresponding chair N-tosylimines-chromenes with excellent enantioselectivity and yield. The reaction tolerates a range of functional groups.

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Key Words

2H-chromenes, organocatalysis

ID: J42-Y2020