Issue 11, 2001

The semi-pinacol rearrangement of homochiral epoxyalcohols catalysed by rare earth triflates

Abstract

α,β-Epoxy ketones, prepared using the polyleucine catalysed asymmetric epoxidation of enones, can be converted into α-substituted β-hydroxy ketones via carbonyl alkylation with Grignard reagents followed by ytterbium triflate catalysed semi-pinacol rearrangement of the resulting epoxyalcohols.

Graphical abstract: The semi-pinacol rearrangement of homochiral epoxyalcohols catalysed by rare earth triflates

Supplementary files

Article information

Article type
Communication
Submitted
27 Feb 2001
Accepted
10 Apr 2001
First published
01 May 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1253-1255

The semi-pinacol rearrangement of homochiral epoxyalcohols catalysed by rare earth triflates

J. F. Bickley, B. Hauer, P. C. A. Pena, S. M. Roberts and J. Skidmore, J. Chem. Soc., Perkin Trans. 1, 2001, 1253 DOI: 10.1039/B101838H

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