Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >
Synthesis of Baylis-Hillman adducts
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Recent Literature
The samarium diiodide promoted addition of α-halo-α,β-unsaturated esters to
carbonyl compounds led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates in
good yields and very high stereoselectivity. A mechanism is proposed to
explain this transformation.
J. M. Concellon, M. Huerta, J. Org. Chem., 2005,
70, 4714-4719.
Silica gel-DABCO catalyzed oxidation of alcohols to aldehydes with chloramine-T
followed by their Morita-Baylis-Hillman reaction with acrylonitrile or methyl
acrylate gives good overall yields of the corresponding Morita-Baylis-Hillman
adducts. The present work opens up a new and efficient synthetic route to
Morita-Baylis-Hillman adducts directly from alcohols in a one-pot operation.
L. D. S. Yadav, V. P. Srivasta, R. Patel, Synlett, 2010,
1047-1050.
Various
ketones as the electrophiles react in a one pot three-component coupling with an aluminum allenoate
intermediate derived from ethyl propiolate and alluminium iodide to yield β-iodo Morita-Baylis-Hillman adducts with high
yield and excellent Z-stereoselectivity.
S. Il Lee, G.-S. Hwang, D. H. Ryu, Synlett, 2007, 59-62.
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.
