Adam Waldemar, Bosio Sara G, Wolff Barbara T
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Org Lett. 2003 Mar 20;5(6):819-22. doi: 10.1021/ol0273194.
[structure: see text] Chiral oxazolidinone-substituted enecarbamates 1 are epoxidized in a diastereoselectivity up to 93:7 for both DMD and mCPBA. The diastereofacial differentiation depends on the steric interaction between the R(1) substituent on the oxazolidinone ring and the incoming electrophile. The stereochemical course of epoxidation was assessed by chemical correlation with the known optically active diols.
[结构：见正文] 手性恶唑烷酮取代的烯氨基甲酸酯1在使用DMD和mCPBA时均以高达93:7的非对映选择性进行环氧化。非对映面的区分取决于恶唑烷酮环上的R(1)取代基与进攻亲电试剂之间的空间相互作用。通过与已知的旋光二醇进行化学关联来评估环氧化的立体化学过程。
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