A convenient method for the synthesis of (Z)-α-haloacrylates: Lewis base-catalyzed carbonyl olefination using α-halo-C,O-bis(trimethylsilyl)ketene acetals

✍ Scribed by Makoto Michida; Takako Toriumi; Teruaki Mukaiyama

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 221 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.02.019

✦ Synopsis

A highly useful method for the stereoselective synthesis of (Z)-a-haloacrylates from various aldehydes that uses a-halogenated ethyl-C,O-bis(trimethylsilyl)ketene acetals in the presence of a Lewis base catalyst such as acetate salts was established. This procedure gives the corresponding a-halo-a,b-unsaturated esters in high yields with excellent stereoselectivity from E/Z mixtures of ketene silyl acetals under mild conditions.