One-Pot Synthesis of alpha-Amino Acids through Carboxylation of Ammonium Ylides with CO2 Followed by Alkyl Migration

摘要

A simple, yet powerful protocol for alpha-amino acid synthesis using carbon dioxide (CO2) was developed. alpha-Amino silanes could undergo four successive reactions (formation of ammonium salt, carboxylation, esterification, and 2,3- or 1,2-Stevens rearrangement) in the presence of allylic or benzylic halides under a CO2 atmosphere (1 atm). It is noteworthy that carboxylation at the position adjacent to a nitrogen atom proceeded via an ammonium ylide intermediate under mild conditions.