Issue 86, 2015

Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde

Abstract

The bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde affords anti-4,5-disubstituted-1,3-dioxolanes in an efficient and stereoselective manner. The reaction provides a practical, inexpensive and atom-economical approach to these types of heterocycles, which represent useful intermediates for target-directed synthesis and precursors to syn-1,2-diols.

Graphical abstract: Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde

Supplementary files

Article information

Article type
Communication
Submitted
07 Mar 2015
Accepted
21 May 2015
First published
14 Sep 2015

Chem. Commun., 2015,51, 15681-15684

Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde

A. Grisin, S. Oliver, M. D. Ganton, J. Bacsa and P. A. Evans, Chem. Commun., 2015, 51, 15681 DOI: 10.1039/C5CC01949D

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