| Control of stereochemistry: a general synthesis of cis- or trans-beta,gamma-disubstituted-gamma-butyrolactones following Z-crotylboration. | |
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MedLine Citation:
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PMID: 16898840 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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[reaction; see text] A general and practical procedure for the highly diastereoselective preparation of either the cis- or trans-beta,gamma-disubstituted-gamma-butyrolactones by appropriate choice of Lewis or Bronsted acid catalysts during crotylboration or lactonization is reported. The cis-stereochemistry of the Z-crotylboration product can be inverted with strong acids during lactonization. A carbocation mechanism and catalytic cycle has been proposed. |
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Authors:
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P Veeraraghavan Ramachandran; Debarshi Pratihar; Debanjan Biswas |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Organic letters Volume: 8 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2006 Aug |
Date Detail:
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Created Date: 2006-08-10 Completed Date: 2007-06-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 3877-9 Citation Subset: - |
Affiliation:
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Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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