An efficient synthesis of pyrazoles from tosylhydrazones and nitroalkenes was developed. In comparison with the previously reported 1,3-dipolar cycloaddition reaction of diazo compounds with electron-deficient alkenes or alkynes, this methodology proceeded with a sequential Baylis-Hillman/intramolecular cyclization mechanism and a variety of reversed regioselectivity products were prepared in g...

A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee.

This work demonstrates that, in accord with metal catalysis, ferrocene could be an excellent scaffold for organocatalysts. The simple and easily accessible bifunctional ferrocene-based squaramide-phosphine shows high enantioselectivity in the intramolecular Morita-Baylis-Hillman reaction of 7-aryl-7-oxo-5-heptenals, giving a variety of 2-aroyl-2-cyclohexenols in up to 96% ee.

One-pot synthesis of substituted pyrroles by a cascade reaction of azides with Morita-Baylis-Hillman acetates of acetylenic aldehydes is described and the reaction is efficiently mediated by triphenyl phosphine at room temperature. Sodium azide is successfully used to provide N-unsubstituted pyrroles, while alkyl azides afforded the corresponding N-alkylated pyrroles through a sequence of allyl...

The kinetic data for a Baylis-Hillman reaction in certain ionic liquids possessing ethylsulfate anion [EtSO(4)](-) demonstrate that the rate determining step (RDS) is second order in aldehyde, but first order in acrylate and DABCO. This observation is similar to the one made by McQuade et al., who carried out this reaction in an aprotic polar solvent like DMSO. However, this is in contrast to t...

An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor...

[reaction: see text] The Morita-Baylis-Hillman reaction of a variety of conjugated nitroalkenes with activated nonenolizable carbonyl compounds such as glyoxylate, trifluoropyruvate, pyruvaldehyde, and ninhydrin in the presence of 40-100 mol % of DMAP in acetonitrile or 100 mol % of imidazole in CHCl(3) or THF provided the adducts in decent to good yields. In most cases, the reactions catalyzed...

Continuing our research on the use of organophosphorus derivatives aziridines in asymmetric synthesis and expanding scope their applicability, chiral aziridine-phosphines obtained earlier laboratory were used as catalysts Morita–Baylis–Hillman reaction methyl vinyl ketone acrylate with various aromatic aldehydes. The desired products formed moderate to high chemical yields enantiomeric excess r...