Catalytic hydrogen transfer: Synthesis of protected cyclic enamines

AEI 83

Andrew D. Bolig, bolig@email.unc.edu, Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599 and Maurice Brookhart, mbrookhart@unc.edu, Department of Chemistry, UNC Chapel Hill, CB# 3290, Chapel Hill, NC 27599-3290.
Transition-metal catalyzed intramolecular hydrogen transfer has been developed into an attractive method for synthesis of reactive olefins from relatively inert, saturated substrates. In particular, protected cyclic enamines and 1,2-diheteroatom alkenes have been synthesized, which are virtually inaccessible by other methodology. Scope, functional group tolerance, selectivity, and further functionalization will be discussed. Rational catalyst design has led to the development of complexes which mediate these transformations with dramatically enhanced rates, under milder conditions.