Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of meso Cyclic Anhydrides

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• 作者：Lin-Jie Yan ; Hai-Feng Wang ; Dr. Wen-Xue Chen ; Yuan Tao ; Kai-Jun Jin and Prof. Fen-Er Chen
• 刊名：ChemCatChem
• 出版年：2016
• 出版时间：July 6, 2016
• 年：2016
• 卷：8
• 期：13
• 页码：2249-2253
• 全文大小：634K
• ISSN：1867-3899

文摘

The synthesis of new chloramphenicol-base-derived thiourea organocatalysts, (1S,2R)-12 a–f and (1R,2R)-15 a–c, and their use in the enantioselective alcoholysis of meso-anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)-12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)-15 a–c. This technique was used to synthesize (R)-(−)-baclofen.