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

作者：Yan, Lin-Jie; Wang, Hai-Feng; Chen, Wen-Xue; Tao, Yuan; Jin, Kai-Jun; Chen, Fen-Er^*

来源：ChemCatChem, 2016, 8(13): 2249-2253.

DOI：10.1002/cctc.201600228

• asymmetric catalysis
• chirality
• enantioselectivity
• organocatalysis
• synthesis design

The synthesis of new chloramphenicol-base-derived thiourea organocatalysts, (1S, 2R)-12a-f and (1R, 2R)-15a-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)-12a-f were used. Almost no enantioselectivities were achieved with the use of (1R, 2R)-15a-c. This technique was used to synthesize (R)-(-)-baclofen.

• 出版日期2016-7-6
• 单位复旦大学