Highly chemoselective direct crossed aliphatic- aromatic acyloin condensations with triazolium-derived carbene catalysts
Citation:
S. E. O'Toole, C. A. Rose, S. Gundala, K. Zeitler and S. J. Connon, Highly chemoselective direct crossed aliphatic- aromatic acyloin condensations with triazolium-derived carbene catalysts, Journal of Organic Chemistry, 76, 2, 2011, 347-357Download Item:
Chemoselective.pdf (Published (author's copy) - Peer Reviewed) 350.2Kb
Abstract:
It has been shown for the first time that triazolium pre-catalysts promote (in the
presence of base) highly chemoselective crossed acyloin condensation reactions between
aliphatic and ortho-substituted aromatic aldehydes. An o-bromine atom can serve as a
temporary directing group to ensure high chemoselectivity (regardless of the nature of the
other substituents on the aromatic ring) which then can be conveniently removed. The
process is of broad scope and is operationally simple as it does not require the preactivation
of any of the coupling partners to ensure selectivtiy. Preliminary data indicates
that highly enantioselective variants of the reaction are feasible using chiral pre-catalysts.
Sponsor
Grant Number
Science Foundation Ireland (SFI)
Irish Research Council for Science and Engineering Technology (IRCSET)
Author's Homepage:
http://people.tcd.ie/connonshttp://people.tcd.ie/gundalas
Description:
PUBLISHED
Author: CONNON, STEPHEN; GUNDALA , SIVAJI
Type of material:
Journal ArticleCollections:
Series/Report no:
Journal of Organic Chemistry76
2
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Full text availableKeywords:
Chemistry, enantioselectiveSubject (TCD):
Nanoscience & MaterialsLicences: