Isomerization of Chiral Non-Racemic α-Substituted Propargylic Amines to Terminal Acetylenes

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols.

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of...

Asymmetric synthesis of substituted NH-piperidines from chiral amines.

Previously, we reported an efficient asymmetric synthesis of substituted piperidines through an exocyclic chirality induced nitroalkene/amine/enone (NAE) condensation reaction. An effective protecting group strategy was developed herein to achieve enantiopure piperidines (yields up to 92%) with complete chirality retention (ee > 95%). A simple derivatization of the obtained piperidines gave thi...

From Racemic Alcohols to Enantiopure Amines: Ru-Catalyzed Diastereoselective Amination

A commercially available ruthenium(II) PNP-type pincer catalyst (Ru-Macho) promotes the formation of α-chiral tert-butanesulfinylamines from racemic secondary alcohols and Ellman's chiral tert-butanesulfinamide via a hydrogen borrowing strategy. The formation of α-chiral tert-butanesulfinylamines occurs in yields ranging from 31% to 89% with most examples giving >95:5 dr.

Copper(I)-Catalyzed Coupling of Terminal Acetylenes with Aryl or Vinyl Halides Copper(I)-Catalyzed Coupling of Terminal Acetylenes

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04609f Click here for additional data file.

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic a-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of...