Department of Materials Chemistry, Faculty of Engineering, Shinshu University , 4-17-1 Wakasato, Nagano 380-8553, Japan.
Org Lett. 2017 Nov 3;19(21):5786-5789. doi: 10.1021/acs.orglett.7b02722.
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.
描述了一系列恶唑烷酮的制备方法，包括对映体富集的 N-芳基取代恶唑烷酮，其中四芳基鏻盐（TAPS）有效地催化了异氰酸酯和环氧化物的[3+2]偶联反应。关键的发现是一种布朗斯台德酸/卤化物离子双功能催化剂，它可以高区域选择性地加速环氧化物开环。机理研究表明，TAPS 生成的叶立德以及卤代醇的形成，在与异氰酸酯的反应中起着关键作用。
