Document Detail


Al-isopropoxydiisobutylalane: a study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction.
MedLine Citation:
PMID:  15609968     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Perdip S Bahia; Matthew A Jones; John S Snaith
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Dec 
Date Detail:
Created Date:  2004-12-21     Completed Date:  2005-03-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9289-91     Citation Subset:  -    
Affiliation:
School of Chemistry, The University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
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