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Highly stereoselective synthesis of anti-N-protected-alpha-amino epoxides
R V Hoffman1, W S Weiner, N Maslouh
1Department of Chemistry and Biochemistry, New Mexico State University, North Horseshoe Drive, Las Cruces, New Mexico 88003-8001, USA. rhoffman@nmsu.edu
The Journal of Organic Chemistry
|August 21, 2001
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.