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Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides

Yasunori Toda*, Shuto Gomyou, Shoya Tanaka, Yutaka Komiyama, Ayaka Kikuchi and Hiroyuki Suga*

*Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan, Email: ytodashinshu-u.ac.jp, sugahioshinshu-u.ac.jp

Y. Toda, S. Gomyou, S. Tanaka, Y. Komiyama, A. Kikuchi, H. Suga, Org. Lett., 2017, 19, 5786-5789.

DOI: 10.1021/acs.orglett.7b02722 (free Supporting Information)



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Abstract

Tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides to provide a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones. These Brønsted acid/halide ion bifunctional catalysts accelerate epoxide ring opening with high regioselectivity.

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proposed mechanism



Key Words

Oxazolidinones, Organocatalysis


ID: J54-Y2017