Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5272830 | Tetrahedron Letters | 2009 | 4 Pages |
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
Rachid Baati, Charles Mioskowski, Dhurke Kashinath, Sanjeevarao Kodepelly, Biao Lu, J.R. Falck,