Highly stereoselective synthesis of anti-N-protected-alpha-amino epoxides.
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.
Hoffman
R V
RV
Department of Chemistry and Biochemistry, New Mexico State University, North Horseshoe Drive, Las Cruces, New Mexico 88003-8001, USA. rhoffman@nmsu.edu
Weiner
W S
WS
Maslouh
N
N
D000596:Amino Acids / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D004852:Epoxy Compounds