STEREOSELECTIVE AND STEREOSPECIFIC SYNTHESIS OF 2-ALKYLIDENE-3-METHYLENE SUCCINIC ACID DIMETHYL ESTERS

Abstract

ABSTRACT 1-Alkyl-2,3-dimethoxycarbonyl-1,3-butadienes 4 were synthesized via two different routes. In the first route, the Wittig-Horner reaction of the readily available phosphonate 2 with various aldehydes yielded the corresponding 1,3-dienes 4 with a good E stereoselectivity. The second route, using α-(bromomethyl) fumarate 1 under basic conditions, provides stereospecifically pure (E)-1,3-dienes 4. STEREOSELECTIVE AND STEREOSPECIFIC SYNTHESIS OF 2-ALKYLIDENE-3-METHYLENE SUCCINIC ACID DIMETHYL ESTERSAll authorsF. Béji, J. Lebreton, J. Villiéras & H. Amrihttps://doi.org/10.1081/SCC-120014031Published online:16 August 2006 Scheme 1. Display full size Scheme 1.