Issue 34, 2006
From the journal:

Chemical Communications

Chiral base mediated transformation of cyclic 1,3-diketones

Benjamin Butler,a   Thomas Schultza  and  Nigel S. Simpkins*a  

* Corresponding authors

a School of Chemistry, The University of Nottingham, University Park, Nottingham, UK
E-mail: Nigel.Simpkins@Nottingham.ac.uk
Fax: +44(0) 115 951 3564
Tel: +44(0) 115 951 3533

Abstract

Treatment of certain 1,3-diketones with a chiral lithium amide base results in the formation of a non-racemic lithium mono-enolate; these intermediates can be transformed directly into chiral hydroxyketone products by reduction with DIBAL-H in high yield and with selectivities of up to 99% ee.

Graphical abstract: Chiral base mediated transformation of cyclic 1,3-diketones

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Article information

DOI
https://doi.org/10.1039/B606864B
Article type
Communication
Submitted
15 May 2006
Accepted
04 Jul 2006
First published
27 Jul 2006

Chem. Commun., 2006, 3634-3636

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Chiral base mediated transformation of cyclic 1,3-diketones

B. Butler, T. Schultz and N. S. Simpkins, Chem. Commun., 2006, 3634 DOI: 10.1039/B606864B

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