An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester
- 11 February 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (6) , 2372-2375
- https://doi.org/10.1021/jo047918j
Abstract
An asymmetric synthesis of (S)-γ-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N‘-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and >97% ee.Keywords
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