Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes

✍ Scribed by Rachid Baati; Charles Mioskowski; Dhurke Kashinath; Sanjeevarao Kodepelly; Biao Lu; J.R. Falck

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 217 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.11.027

✦ Synopsis

Methyl (Z)-a-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 CrCl 2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatskytype addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.