| Stereoconvergent approach for synthesizing enantiopure 5, 6-dialkylpipecolic acids. | |
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MedLine Citation:
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PMID: 10824154 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Investigating a general route for synthesizing pipecolic acid ) piperidine-2-carboxylic acid ( derivatives with substituents at the 3-, 4-, 5- and 6-position, we discovered a stereoconvergent process that provides an effective means for making 5, 6-dialkyl-epsilonpipecolate (Scheme 1, PhF = 9-phenylfluoren-9-yl). Hydrogenation of diastereomeric mixtures of gamma-oxo gamma-hydroxy and gamma-acetoxy alpha-N-(PhF)amino tert-butyl esters causes the eventual loss of the gamma-substituent to furnish an azadiene intermediate that can reduce diastereoselectively to 5, 6-dialkylpipecolate having the all cis relative stereoconfiguration. Five enantiopure (>94% ee) 5,6-dialkylpipecolic acids were synthesized, employing aspartic acid as an inexpensive chiral educt in this process. |
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Authors:
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M E Swarbrick; W D Lubell |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chirality Volume: 12 ISSN: 0899-0042 ISO Abbreviation: Chirality Publication Date: 2000 Jun |
Date Detail:
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Created Date: 2004-01-22 Completed Date: 2004-02-17 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8914261 Medline TA: Chirality Country: United States |
Other Details:
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Languages: eng Pagination: 366-73 Citation Subset: IM |
Copyright Information:
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Copyright 2000 Wiley-Liss, Inc. |
Affiliation:
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Departement de Chimie, Universite de Montreal, Montreal, Quebec, Canada. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Aspartic Acid
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chemistry* Chemistry / methods Ketones / chemistry Models, Chemical Pipecolic Acids / chemical synthesis*, chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Ketones; 0/Pipecolic Acids; 56-84-8/Aspartic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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