Conjugate addition/Ireland-Claisen rearrangements of allyl fumarates: simple access to terminally differentiated succinates.
The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland-Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon-carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.
Bausch
Cory C
CC
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Johnson
Jeffrey S
JS
D005650:Fumarates / Q000737:chemistry*; D008958:Models, Molecular; D013386:Succinates / Q000737:chemistry*
D005650:Fumarates; D013386:Succinates