Syn-Selective Synthesis of β-Branched α-Amino Acids by Alkylation of Glycine-Derived Imines with Secondary Sulfonates

• DOI: 10.1021/acs.orglett.5b02448
• Publication Date: 2015-10-07T13:52:28Z
• Authors: Sha Lou; Grace M. McKenna; Steven A. Tymonko; Antonio Ramirez; Tamas Benkovics; David A. Conlon; Francisco Gonzále...
• Keywords: Imine; Protecting group

A syn-selective synthesis of β-branched α-amino acids has been developed based on the alkylation glycine imine esters with secondary sulfonates. The potassium counterion for enolate, solvent, and leaving group electrophile were key levers to maximize diasteroselectivity alkylation. optimized conditions enabled a straightforward preparation number that can be challenging obtain.