Highly Stereoselective Synthesis of anti-N-Protected-α-Amino Epoxides
- 1 August 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (17) , 5790-5795
- https://doi.org/10.1021/jo010319h
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 β-ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.Keywords
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