Document Detail


Enantioselective synthesis of α-fluoro-β(3)-amino esters: synthesis of enantiopure, orthogonally protected α-fluoro-β(3)-lysine.
MedLine Citation:
PMID:  20931997     Owner:  NLM     Status:  In-Process    
Abstract/OtherAbstract:
The scope of a tandem conjugate addition-fluorination sequence performed on α,β-unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(α-methylbenzyl)amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, α-fluoro-β(3)-amino esters can be obtained in up to quantitative yield and 80:20 to >99:1 dr. This simple methodology does not rely on the use of α-amino acids from the chiral pool and thus provides the potential for the preparation of enantiopure α-fluoro-β(3)-amino acids with a wide variety of side chains. Its utility was demonstrated through the synthesis of orthogonally protected (2S,3S)-α-fluoro-β(3)-lysine.
Authors:
Peter J Duggan; Martin Johnston; Taryn L March
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-10-29     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7365-72     Citation Subset:  -    
Affiliation:
CSIRO Materials Science and Engineering, Bag 10, Clayton South, Victoria 3169, Australia. peter.duggan@csiro.au
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