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

ChemCatChem ◽  
2016 ◽  
Vol 8 (13) ◽  
pp. 2249-2253 ◽  
Author(s):  
Lin-Jie Yan ◽  
Hai-Feng Wang ◽  
Wen-Xue Chen ◽  
Yuan Tao ◽  
Kai-Jun Jin ◽  
...  
Keyword(s):  
Enantioselective Alcoholysis

scholarly journals Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

2018 ◽  
Vol 14 ◽  
pp. 309-317 ◽  
Author(s):  
Lingjun Xu ◽  
Shuwen Han ◽  
Linjie Yan ◽  
Haifeng Wang ◽  
Haihui Peng ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Asymmetric Synthesis ◽  
Hydrogen Bond Donor ◽  
Cyclic Anhydrides ◽  
Enantioselective Alcoholysis

A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

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