A Highly Enantioselective Intramolecular Heck Reaction with a Monodentate Ligand

A highly enantioselective intramolecular Heck reaction with a monodentate ligand.

An efficient enantioselective intramolecular Heck reaction of cyclohexadienones, using readily available and modular TADDOL-based mono- and bidentate phosphoramidites as chiral ligands and not requiring any additives, has been developed. Excellent enantioselectivities up to 96% ee are reached for the first time in a Heck reaction with monodentate ligands.

A highly enantioselective catalytic intramolecular Stetter reaction.

A family of chiral triazolium salts has been developed for inducing the asymmetric intramolecular Stetter reaction. The use of an aminoindanol-derived catalyst affords optimal results, with the product keto esters formed in 82-97% ee and very good chemical yield. Aromatic and aliphatic aldehydes are equally competent substrates for this reaction. The reaction conditions are reasonably mild and ...

Cysteine-derived organocatalyst in a highly enantioselective intramolecular Michael reaction.

Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.

Ligand-free palladium-catalyzed intramolecular Heck reaction of secondary benzylic bromides.

A facile ligand-free palladium-catalyzed intramolecular Heck reaction of β-hydrogen-containing secondary benzylic bromides was developed, which affords pyrroline derivatives with good regioselectivities.

The asymmetric intramolecular Heck reaction in natural product total synthesis.