Article ID Journal Published Year Pages File Type
5272830 Tetrahedron Letters 2009 4 Pages PDF
Abstract

Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.

Graphical abstractDownload full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
Authors
, , , , , ,