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Catalytic Asymmetric Darzens‐Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides
Author(s) -
Nam Dong Guk,
Shim Su Yong,
Jeong HyeMin,
Ryu Do Hyun
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202108454
Subject(s) - enantioselective synthesis , chemistry , catalysis , ketone , lewis acids and bases , glyoxal , organic chemistry , yield (engineering) , epoxy , combinatorial chemistry , materials science , metallurgy
Highly enantioselective Darzens‐type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β‐epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio‐ and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ‐butyrolactone, tertiary β‐hydroxy ketone and epoxy diester.