An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester
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‘-dibromodimethylh...
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| Published in | Journal of organic chemistry Vol. 70; no. 6; pp. 2372 - 2375 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
18.03.2005
Amer Chemical Soc |
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| 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. |
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| AbstractList | [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. [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. 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. 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. |
| Author | Gauthier, Donald R. Limanto, John Desmond, Richard A. Shafiee, Ali Devine, Paul N. Volante, R. P. Reamer, Robert A. Foster, Bruce R. Upadhyay, Veena |
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| Cites_doi | 10.1021/ol027229z 10.1021/jo035488b 10.1016/j.tet.2004.05.051 10.1016/j.tetlet.2003.12.102 10.1016/S0040-4039(98)01995-9 10.1021/ja00168a046 10.1021/jo00064a010 10.1016/S0040-4020(98)01064-3 10.1016/0040-4039(94)02408-4 10.1016/S0960-894X(01)80127-X |
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| Keywords | IMIDATE SALTS ASYMMETRIC-SYNTHESIS ENANTIOSELECTIVE SYNTHESIS N-METHYLACETIMIDATE ALKYLATION PHASE-TRANSFER CATALYSIS ALPHA-AMINO-ACIDS DIASTEREOSELECTIVE SYN-EPOXIDATION STEREOSELECTIVE-SYNTHESIS DYNAMIC KINETIC RESOLUTION Catalytic reaction Ethanol Enzyme Triacylglycerol lipase Esterases Leucine Ring cleavage Carboxylic ester hydrolases Ester Enzymatic method Asymmetric synthesis Aminoacid Hydrolases Carboxamide Enantiomeric excess Fluorine Organic compounds |
| Language | English |
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| Snippet | An asymmetric synthesis of (S)-γ-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of... An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of... [reaction: see text] An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic... |
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| SubjectTerms | Aliphatic compounds Catalysis Chemistry Chemistry, Organic Exact sciences and technology Glycosphingolipids - chemical synthesis Lipase - chemistry Molecular Conformation Organic chemistry Physical Sciences Preparations and properties Science & Technology Stereoisomerism |
| Title | An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester |
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