Synthesis of [2.2]Paracyclophane-Based Glycidic Amides Using Chiral Ammonium Ylides,Helvetica Chimica Acta

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Synthesis of [2.2]Paracyclophane-Based Glycidic Amides Using Chiral Ammonium Ylides
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2021-06-07 , DOI: 10.1002/hlca.202100073
David Weinzierl ₁ , Mario Waser ₂

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An ammonium ylide-mediated stereoselective protocol for the synthesis of a series of novel [2.2]paracyclophane-based epoxides starting from racemic 4-formyl[2.2]paracyclophane has been developed. By using achiral ammonium salts as ylide precursors, the corresponding epoxide products were obtained in isolated yields up to 76 % and with diastereoselectivities up to d.r.=9 : 1. When carrying out the reaction with chiral ammonium salts instead, the products were accessible with e.r.>93.5 : 6.5 and d.r.>3 : 1, accompanied with a moderately enantioselective kinetic resolution of the racemic starting aldehyde (e.r.=75 : 25).

中文翻译：

使用手性叶立德铵合成 [2.2] 对环芳基缩水甘油酰胺

已经开发了一种用于从外消旋 4-甲酰基 [2.2] 对环烷开始合成一系列新型 [2.2] 对环芳基环氧化物的铵叶立德介导的立体选择性方案。通过使用非手性铵盐作为叶立德前体，以高达 76 % 的分离产率和高达 9 : 1 的非对映选择性获得了相应的环氧化物产物。 > 93.5 : 6.5 和 dr > 3 : 1，伴随着外消旋起始醛的适度对映选择性动力学拆分（er = 75 : 25）。

更新日期：2021-07-16

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