Conjugate Addition/Ireland-Claisen
Rearrangements of Allyl Fumarates: Simple
Access to Terminally Differentiated Succinates
Cory C. Bausch andJeffrey S. Johnson*
Department of Chemistry, University of North Carolina at
Chapel Hill, Chapel Hill, North Carolina 27599-3290
jsj@unc.edu
Received October 19, 2007
Abstract:
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.
