Asymmetric synthesis of alpha-methylphosphophenylalanine derivatives using sulfinimine-derived enantiopure aziridine-2-phosphonates.
[formula: see text] 2-Methylaziridine-2-phosphonates were prepared from enantiopure sulfinimines and were demonstrated to be versatile synthetic intermediates for the synthesis of novel alpha-disubstituted and alpha,beta-trisubstituted alpha-aminophosphonate derivatives. The first asymmetric synthesis of both enantiomers of alpha-methylphosphophenylalanine is described.
Davis
F A
FA
Department of Chemistry, Temple University, Philadelphia Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
McCoull
W
W
Titus
D D
DD
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
D007097:Imines; D010721:Phosphinic Acids; D013457:Sulfur Compounds; C409507:methylphosphophenylalanine; D000409:Alanine