Organocatalytic formal [4 + 2] cycloaddition of o-quinone-methyl derivatives and 2-isocyanatomalonate diesters for the construction of chroman derivatives with adjacent quaternary chiral centers

An asymmetric organocatalytic formal [4 + 2] cycloaddition/annulation cascade of ortho-quinone methides with 2-isocyanatomalonate diesters has been reported. Chromans bearing three contiguous stereogenic centers with a chiral orthoester skeleton were obtained in high yields with excellent enantio- a...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-05, Vol.11 (10), p.2917-2921
Main Authors: Xiong, Tong, Yi-Zhao, Xu, Wang, Yao, You-Cai, Xiao, Chen, Fen-Er
Format: Article
Language:English
Subjects:
Catalysts
Chemical reactions
Cycloaddition
Diesters
Quinones
Urea
Online Access:Get full text
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Summary:An asymmetric organocatalytic formal [4 + 2] cycloaddition/annulation cascade of ortho-quinone methides with 2-isocyanatomalonate diesters has been reported. Chromans bearing three contiguous stereogenic centers with a chiral orthoester skeleton were obtained in high yields with excellent enantio- and diastereoselectivities (up to 93% yield, 99% ee and >20 : 1 dr) by using a tertiary amino-urea catalyst.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo00141a