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: ytoda
shinshu-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
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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
Y. Toda, K. Hashimoto, Y. Mori, H. Suga, J. Org. Chem., 2020, 85, 10980-10987.
Key Words
Oxazolidinones, Organocatalysis
ID: J54-Y2017
