Enantioselective Synthesis of α‐Fluorinated β‐Amino Acid Derivatives

by an Asymmetric Mannich Reaction and Selective Deacylation/Decarboxylation Reactions

Yuanhang Pan, Yujun Zhao, Ting Ma, Yuanyong Yang, Hongjun Liu, Zhiyong Jiang Prof. Dr., Choon‐Hong Tan Prof. Dr.

Chemistry - An European Journal, 2010, 16, 779 – 782

Abstract: Useful degradation: A highly enantio‐ and diastereoselective guanidine‐catalyzed Mannich reaction was developed with α‐fluoro‐β‐keto acyloxazolidinone as the fluorocarbon nucleophile (see scheme). α‐Fluoro‐β‐amino ester and α‐fluoro‐β‐amino ketones with chiral fluorinated carbon were obtained by selective deacylation and decarboxylation reactions, respectively.

Paper download: https://doi.org/10.1002/chem.200902830