Issue 46, 2013

Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates

Abstract

An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol condensation. Besides being an expedient synthetic procedure, the ready availability of diverse α-haloacetates, exceptional stereoselectivity, and high yields make the process a versatile transformation in organic synthesis. The potential of this method in up-scaling operations has been illustrated.

Graphical abstract: Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates

Supplementary files

Article information

Article type
Paper
Submitted
04 Aug 2013
Accepted
03 Oct 2013
First published
03 Oct 2013

Org. Biomol. Chem., 2013,11, 8065-8072

Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates

J. K. Augustine, A. Bombrun, S. Venkatachaliah and A. Jothi, Org. Biomol. Chem., 2013, 11, 8065 DOI: 10.1039/C3OB41592A

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