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Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones

Author:
Zhang, Zhi-Pei, Xie, Kai-Xue, Yang, Chen, Li, Man, Li, Xin
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 364-373
ISSN:
1520-6904
Subject:
chemical reactions, chemical structure, diastereoselectivity, enantioselectivity, organic chemistry, organic compounds
Abstract:
A chiral phosphoric acid-catalyzed approach constructing dihydrocoumarin motifs by the addition of azlactones to para-quinone methides (p-QMs) was developed. The reaction proceeded smoothly with a wide range of p-QMs and azlactones to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the stereoselectivity.
Agid:
6046736