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Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides

Author:
Toda, Yasunori, Gomyou, Shuto, Tanaka, Shoya, Komiyama, Yutaka, Kikuchi, Ayaka, Suga, Hiroyuki
Source:
Organic letters 2017 v.19 no.21 pp. 5786-5789
ISSN:
1523-7052
Subject:
Bronsted acids, catalysts, chemical reactions, chemical structure, epoxides, oxazolidinones, regioselectivity, salts
Abstract:
Preparation of a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones, in which tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides effectively, is described. The key finding is a Brønsted acid/halide ion bifunctional catalyst that can accelerate epoxide ring opening with high regioselectivity. Mechanistic studies disclosed that the ylide generated from TAPS, along with the formation of halohydrins, plays a crucial role in the reaction with isocyanates.
Agid:
5851272