Palladium-catalyzed Asymmetric Heck Reaction Research Articles

Pd-Catalyzed Enantioselective Heck Reaction of Aryl Triflates and Alkynes.

The first palladium-catalyzed asymmetric Heck reaction between aryl triflates and alkynes to give trisubstituted allenes with high er under mild reaction conditions is described. The key to the success is the discovery and fine-tuning of the different N-substituents of Xu-Phos, which ensure the enantioselectivity and reactivity. Synthetic transformation of the chiral allenes with high chirality transfer was also demonstrated.

Synthesis of Cyclobutenes via a Palladium-Catalyzed Asymmetric Heck Reaction

Synthesis of Cyclobutenes via a Palladium-Catalyzed Asymmetric Heck Reaction

ChemInform Abstract: Kinetic Resolution of 2‐Substituted‐2,3‐dihydrofurans by a Palladium‐Catalyzed Asymmetric Heck Reaction.

The kinetic resolution of 2-substituted-dihydrofurans via a palladium-catalyzed asymmetric Heck reaction was realized, providing optically active 2-substituted-dihydrofurans and trans-2,5-disubstituted-dihydrofurans in high yield and good enantioselectivities with an S factor up to 70.

Kinetic resolution of 2-substituted-2,3-dihydrofurans by a palladium-catalyzed asymmetric Heck reaction

The kinetic resolution of 2-substituted-dihydrofurans via a Pd-catalyzed asymmetric Heck reaction was realized for the first time.

Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3′-disubstituted derivatives

The Ullmann coupling of 1 (R = H) gives a 2:1 mixture of diastereomers 2 (R = H) in 81% yield that are easily separated by silica gel chromatography. This procedure avoids the generally cumbersome and sometimes difficult resolution step with DBTA. Similar Ullmann couplings and separation of the corresponding diastereomers are employed with other derivatives of 1 (R = O tBu, iPr, Ph, and mesityl) ultimately affording a new series of 3,3′-disubsituted-MeO-BIPHEP derivatives. The use of these new derivatives in palladium-catalyzed asymmetric Heck reaction, Pd-catalyzed polyene cyclizations and rhodium-catalyzed hydrogenations is also reported.

ChemInform Abstract: An Efficient Phosphorus-Containing Oxazoline Ligand Derived from cis-2-Amino-3,3-dimethyl-1-indanol: Application to the Palladium-Catalyzed Asymmetric Heck Reaction.

Abstract Enantiopure 2-[2-(diphenylphosphino)phenyl]oxazoline, derived from a non-natural chiral aminoalcohol, cis -2-amino-3,3-dimethyl-1-indanol, was found to be an efficient ligand for the palladium-catalyzed asymmetric Heck reaction.

An efficient phosphorus-containing oxazoline ligand derived from cis-2-amino-3,3-dimethyl-1-indanol: application to the palladium-catalyzed asymmetric Heck reaction

Enantiopure 2-[2-(diphenylphosphino)phenyl]oxazoline, derived from a non-natural chiral aminoalcohol, cis-2-amino-3,3-dimethyl-1-indanol, was found to be an efficient ligand for the palladium-catalyzed asymmetric Heck reaction.