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Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines.

Authors
  • Malkov, Andrei V
  • Stewart-Liddon, Angus J P
  • McGeoch, Grant D
  • Ramírez-López, Pedro
  • Kočovský, Pavel
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Jul 07, 2012
Volume
10
Issue
25
Pages
4864–4877
Identifiers
DOI: 10.1039/c2ob25472g
PMID: 22595994
Source
Medline
License
Unknown

Abstract

A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee).

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