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STEREOSELECTIVE AND STEREOSPECIFIC SYNTHESIS OF 2-ALKYLIDENE-3-METHYLENE SUCCINIC ACID DIMETHYL ESTERS
Journal article   Peer reviewed

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

F. Béji, J. Lebreton, J. Villiéras and H. Amri
Synthetic communications, Vol.32(21), pp.3273-3278
01/01/2002

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.

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