Acidity-Directed Synthesis of Substituted γ-Butyrolactones from Aliphatic Aldehydes

P. Veeraraghavan Ramachandran* and Debarshi Pratihar
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084
Org. Lett., 2007, 9 (11), pp 2087–2090
DOI: 10.1021/ol0705806
Publication Date (Web): May 1, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, chandran@purdue.edu

Abstract

Abstract Image

The strength of the Lewis or Brønsted acids controls the formation of either β,γ-disubstituted-α-methylene-γ-butyrolactones or γ-substituted-α-alkylidene-γ-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.

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History

  • Published In Issue May 24, 2007
  • Received March 8, 2007

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