title: Highly stereoselective synthesis of anti-N-protected-alpha-amino epoxides.
abstract: A simple and efficient method for the synthesis of anti-N-protected amino epoxides from carbamate-protected amino acids is described. The two key steps are the monobromination of a beta-ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, North Horseshoe Drive, Las Cruces, New Mexico 88003-8001, USA. rhoffman@nmsu.edu
authors.forename: R V
authors.initials: RV
authors.lastname: Hoffman
authors.forename: W S
authors.initials: WS
authors.lastname: Weiner
authors.forename: N
authors.initials: N
authors.lastname: Maslouh
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004852:Epoxy Compounds