Organic Chemistry Portal >
Reactions > Organic Synthesis Search

Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >

Synthesis of α,β-unsaturated compounds



Synthesis of

Baylis-Hillman Adducts

Recent Literature

A nickel(0)-catalyzed coupling of α-olefins and isocyanates in the presence of an N-heterocyclic carbene ligand proceeds preferentially at the 2-position of the olefin to provide α,β-unsaturated amides. N-tert-butyl amide products can be converted to the corresponding primary amides under acidic conditions.
K. D. Schleicher, T. F. Jamison, Org. Lett., 2007, 9, 875-878.

A P-cyclohexyl substituted ferrocenophane catalyst affords high levels of asymmetric induction in the organocatalytic [3 + 2] annulation reaction between allenes and electron-poor olefins.
A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, J. Am. Chem. Soc., 2008, 130, 14030-14031.

A nucleophile-catalyzed asymmetric [3+2] cycloaddition of allenes with enones is described. The method has also been applied to reactions of trisubstituted olefins, thereby generating quartenary and tertiary stereocenters.
J. E. Wilson, G. C. Fu, Angew. Chem. Int. Ed., 2006, 45, 1426-1429.