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Conjugate Addition/Ireland−Claisen Rearrangements of Allyl Fumarates:  Simple Access to Terminally Differentiated Succinates

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journal contribution
posted on 15.02.2008, 00:00 authored by Cory C. Bausch, Jeffrey S. Johnson
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.