An efficient chemoenzymatic approach to (S)-gamma-fluoroleucine ethyl ester |
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| Authors: | Limanto John Shafiee Ali Devine Paul N Upadhyay Veena Desmond Richard A Foster Bruce R Gauthier Donald R Reamer Robert A Volante R P |
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| Institution: | Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. john_limanto@merck.com |
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| Abstract: | reaction: see text] An asymmetric synthesis of (S)-gamma-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. |
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