Enantioselective Synthesis of α-Fluorinated β2-Amino Acids

A methodology for the enantioselective synthesis of α-fluorinated β2-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective fluorination and alkylation gave 7 in high diastereomeric excess (>95%). Subseque...

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Bibliographic Details
Published in:Organic letters 2008-03, Vol.10 (5), p.885-887
Main Authors: Edmonds, Michael K, Graichen, Florian H. M, Gardiner, James, Abell, Andrew D
Format: Article
Language:English
Online Access:Get full text
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Summary:A methodology for the enantioselective synthesis of α-fluorinated β2-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective fluorination and alkylation gave 7 in high diastereomeric excess (>95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active α-fluorinated β2-amino acids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol703045z