A Copper(II)-Mediated Regioselective Cyclization−Acetoxylation of 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes

This paper describes a copper(II) acetate-mediated cyclization−acetoxylation of 6,8-dien-1-ones in the presence of sodium acetate as base. A variety of functionalized cyclopentanes containing synthetic useful allylic alcohol moieties with three contiguous stereogenic centers were synthesized in moderate to good yields with moderate to high regioselectivities

Development of Binaphthyl-Based Chiral Dienes for Rhodium(I)-Catalyzed Asymmetric Arylation of <i>N</i>,<i>N</i>-Dimethylsulfamoyl-Protected Aldimines

A variety of binaphthyl-based chiral dienes were synthesized and utilized as steering ligands for the enantioselective arylation of N,N-dimethylsulfamoyl-protected aldimines with arylboronic acids, and moderate to good yields and up to 84% ee were achieved

A Copper(II)-Mediated Regioselective Cyclization−Acetoxylation of 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes

This paper describes a copper(II) acetate-mediated cyclization−acetoxylation of 6,8-dien-1-ones in the presence of sodium acetate as base. A variety of functionalized cyclopentanes containing synthetic useful allylic alcohol moieties with three contiguous stereogenic centers were synthesized in moderate to good yields with moderate to high regioselectivities

Enantioselective Catalysis of Hetero Diels−Alder Reaction and Diethylzinc Addition Using a Single Catalyst

Integration of two asymmetric reactions in one pot with the promotion of a single catalyst has been achieved in high efficiency and excellent stereoselectivity for hetero Diels−Alder reaction of Danishefsky's diene and diethylzinc addition to aldehydes. The strategy described in the present work demonstrated the ability of a single catalyst to promote two distinct enantioselective reactions in one pot

Pd-Catalyzed Asymmetric Allylic Alkylations of 3‑Substituted Indoles Using Chiral P/Olefin Ligands

A palladium-catalyzed asymmetric allylic alkylation of 3-substituted indoles using P/olefin ligands was successfully achieved to afford a variety of indolenines containing a quaternary carbon stereocenter in high yields with up to 87% ee. Significantly, this reaction provides a concise access to a stereoisomer of the natural product Angelicastigmin

Development of Chiral Terminal-Alkene−Phosphine Hybrid Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions

A variety of novel chiral terminal-alkene−phosphine hybrid ligands were successfully developed from diethyl l-tartrate for palladium-catalyzed asymmetric allylic alkylations, etherifications, and amination to give the desired products in excellent yields and ee’s

Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines

A metal-free hydrogenation of 2,4-disubstituted quinolines was realized for the first time using chiral diene derived borane catalysts to furnish the corresponding tetrahydroquinolines in 75–98% yields with 95/5−99/1 dr’s and 86–98% ee’s. This catalytic system was also effective for 2,3-disubstituted quinolines to give moderate to good ee’s

Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines

A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB­(C₆F₅)₂ via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities

Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines

A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB­(C₆F₅)₂ via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities

Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds

A highly enantioselective hydrosilylation of 1,2-dicarbonyl compounds was successfully realized for the first time utilizing the combination of tricyclohexylphosphine and chiral alkenylborane derived <i>in situ</i> from diyne as a frustrated Lewis pair catalyst. A variety of optically active α-hydroxy ketones and esters were obtained in 52–98% yields with 86–99% ee’s