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Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides

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Abstract

A catalytic asymmetric synthesis of 3,4-dihydrocoumarins with adjacent tertiary–quaternary stereocenters by 1,6-addition/transesterification cascade reaction of α-isocyanoacetates with ortho-hydroxyphenyl-substituted para-quinone methides (p-QMs) has been developed. Using a combination of dihydroquinidine-derived aminophosphine and silver nitrate as a binary catalytic system, moderate to good yields, excellent diastereoselectivities (>20 : 1 dr) and good to excellent enantioselectivities (up to 94% ee) were achieved for a wide range of isocyanoacetates and p-QMs.

Graphical abstract: Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides

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Article information


Submitted
13 Dec 2019
Accepted
31 Jan 2020
First published
01 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides

M. Zhao, J. Xiang, Z. Zhao, X. Zhao and M. Shi, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02652E

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