5 years ago

Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides

Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides
Hiroyuki Suga, Yasunori Toda, Shoya Tanaka, Yutaka Komiyama, Ayaka Kikuchi, Shuto Gomyou
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02722

DOI: 10.1021/acs.orglett.7b02722

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