title: Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of alpha-alkyl alpha-amino acids.
abstract: Addition of Et(2)AlCN and i-PrOH to ketosulfinimines (N-sulfinyl imines) affords corresponding alpha-alkyl alpha-amino nitriles in moderate to good yields. The diastereoselectivity is largely dependent on the E/Z isomer ratio of the ketosulfinimine. Hydrolysis of the diastereomerically pure amino nitriles affords enantiopure alpha-alkyl alpha-amino acids in moderate to good yields.
authors: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
authors: F A
authors: FA
authors: Davis
authors: S
authors: S
authors: Lee
authors: H
authors: H
authors: Zhang
authors: D L
authors: DL
authors: Fanelli
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D007097:Imines; D013452:Sulfonium Compounds