Highly stereoselective synthesis of anti-N-protected-alpha-amino epoxides |
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| Authors: | Hoffman R V Weiner W S Maslouh N |
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| Affiliation: | Department of Chemistry and Biochemistry, New Mexico State University, North Horseshoe Drive, Las Cruces, New Mexico 88003-8001, USA. rhoffman@nmsu.edu |
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| 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. |
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