Document Detail

Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid.
MedLine Citation:
PMID:  15455148     Owner:  NLM     Status:  MEDLINE    
The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-[small alpha]-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and trans-(3R,4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.
Mark E Bunnage; Stephen G Davies; Paul M Roberts; Andrew D Smith; Jonathan M Withey
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2004-09-01
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  2     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2004 Oct 
Date Detail:
Created Date:  2004-09-29     Completed Date:  2006-05-17     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  2763-76     Citation Subset:  IM    
Copyright Information:
Copyright 2004 The Royal Society of Chemistry
Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK.
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MeSH Terms
Carboxylic Acids / chemical synthesis*,  chemistry*
Furans / chemical synthesis*,  chemistry*
Models, Molecular
Molecular Structure
Pyrrolidines / chemical synthesis*,  chemistry*
Reg. No./Substance:
0/4-aminopyrrolidine-3-carboxylic acid; 0/4-aminotetrahydrofuran-3-carboxylic acid; 0/Carboxylic Acids; 0/Furans; 0/Pyrrolidines

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