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Acidity-directed synthesis of substituted gamma-butyrolactones from aliphatic aldehydes.
MedLine Citation:
PMID:  17469835     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The strength of the Lewis or Brønsted acids controls the formation of either beta,gamma-disubstituted-alpha-methylene-gamma-butyrolactones or gamma-substituted-alpha-alkylidene-gamma-butyrolactones via the lactonization or oxonia cope rearrangement-lactonization, respectively, of the borate intermediates resulting from the crotylboration of aliphatic aldehydes with ester-containing crotylboronates, such as (E)-methyl 2-boramethyl-2-butenoates.
Authors:
P Veeraraghavan Ramachandran; Debarshi Pratihar
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Publication Detail:
Type:  Journal Article     Date:  2007-05-01
Journal Detail:
Title:  Organic letters     Volume:  9     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2007 May 
Date Detail:
Created Date:  2007-05-17     Completed Date:  2007-07-24     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2087-90     Citation Subset:  -    
Affiliation:
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu
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