| 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 |
Abstract/OtherAbstract:
|
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. |
| | |
Authors:
|
Mark E Bunnage; Stephen G Davies; Paul M Roberts; Andrew D Smith; Jonathan M Withey |
Related Documents
:
|
18855448 - A nonsymmetric pincer-catalyzed suzuki-miyaura arylation of benzyl halides and other no... 22703818 - Repair of ectopia cordis using a resorbable poly-l-lactic-polyglycolic acid plate in a ... 12510318 - Sulfonamides as novel terminators of cationic cyclisations. 17330168 - Integrated microreaction system for optical resolution of racemic amino acids. 3691518 - Structure of the capsular polysaccharide of haemophilus pleuropneumoniae serotype 5. 16659768 - Abscisic acid metabolism by a cell-free preparation from echinocystis lobata liquid end... |
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 |
Affiliation:
|
Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Carboxylic Acids
/
chemical synthesis*,
chemistry* Furans / chemical synthesis*, chemistry* Models, Molecular Molecular Structure Pyrrolidines / chemical synthesis*, chemistry* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
|
0/4-aminopyrrolidine-3-carboxylic acid; 0/4-aminotetrahydrofuran-3-carboxylic acid; 0/Carboxylic Acids; 0/Furans; 0/Pyrrolidines |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Monomeric analogues of halocidin.
Next Document: Synthesis and binding properties of calix[4]arenes with [2 + 2'] mixed ligating functional groups.