Schoumacker Sébastien, Hamelin Olivier, Téti Sébastien, Pécaut Jacques, Fontecave Marc
Laboratoire de Chimie et Biochimie des Centres Rédox Biologiques, DRDC-CB, UMR 5047 Université Joseph Fourier/CEA/CNRS, CEA Grenoble, 17 avenue des Martyrs, 38054 Grenoble Cedex, France.
J Org Chem. 2005 Jan 7;70(1):301-8. doi: 10.1021/jo048380k.
The preparation of new and easily accessible chiral N-alkyloxaziridines for asymmetric sulfides oxidation was investigated. Most significantly, we report here that inert N-alkyloxaziridines can be activated by Lewis acids to achieve a fast, selective, and efficient oxygen atom transfer to sulfides. Asymmetric sulfoxidation by three new chiral oxaziridines (two of them were structurally characterized by X-ray analysis) afforded enantioselectivities ranging from 22% to 63% ee with the simplest aryl alkyl sulfides.
研究了用于不对称硫化物氧化的新型且易于制备的手性N-烷基氧杂环丁烷的制备。最重要的是，我们在此报告，惰性N-烷基氧杂环丁烷可被路易斯酸活化，以实现向硫化物的快速、选择性和高效的氧原子转移。三种新型手性氧杂环丁烷（其中两种通过X射线分析进行了结构表征）对最简单的芳基烷基硫化物进行不对称硫氧化，对映体选择性范围为22%至63%ee。
