| Al-isopropoxydiisobutylalane: a study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction. | |
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MedLine Citation:
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PMID: 15609968 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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The effect of solvent on the rate and stereoselectivity of cyclic ketone reduction by Al-isopropoxydiisobutylalane (DIBA(i)OPr) has been investigated. In dichloromethane, DIBA(i)OPr behaves as a bulky reducing agent, approaching the carbonyl group along an equatorial trajectory to produce the axial alcohol with >10:1 stereoselectivity. In sharp contrast, reduction in toluene gives the complementary outcome, affording the thermodynamically more stable isomer with >99:1 stereoselectivity. |
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Authors:
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Perdip S Bahia; Matthew A Jones; John S Snaith |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Dec |
Date Detail:
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Created Date: 2004-12-21 Completed Date: 2005-03-30 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 9289-91 Citation Subset: - |
Affiliation:
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School of Chemistry, The University of Birmingham, Edgbaston, Birmingham B15 2TT, UK. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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