Diastereo- and Enantioselective Catalytic Kinetic Resolution of 2-Substituted 3-Nitro-2H-chromenes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

An unprecedented catalytic kinetic resolution of 2-substituted 3-nitro-2H-chromenes via Rh-catalyzed asymmetric hydrogenation has been developed to simultaneously produce a variety syn-chiral 3-nitro-2H-chromanes containing vicinal stereogenic centers with excellent diastero- and enantioselectivities [diastereomeric ratio (dr) >99:1 up 99.9% enantiomeric excess (ee)] recovered chiral 90–99.9% ee in high yields, respectively, achieving selectivity factors 1057. Moreover, addition 3-nitro-2H-chromanes, this new approach provides concise, atom-economical, straightforward access anti-chiral mammalian target rapamycin (mTOR) inhibitor, (R)-DHM25.

Language: Английский

Asymmetric Synthesis of Benzofuranones with a C3 Quaternary Center via an Addition/Cyclization Cascade Using Noncovalent N-Heterocyclic Carbene Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 3, 2024

An asymmetric addition/cyclization cascade of amidoesters and iminoquinones is developed using noncovalent N-heterocyclic carbene (NHC) catalysis. The process enables access to various functionalized benzofuranones with an all-carbon quaternary stereocenter high yields ee values. reaction displays a broad substrate scope. Via product modifications, enantioenriched synthesis biologically relevant spirocyclic lactones lactams achieved. Substrate activation via interaction NHC suggested for the process.

Language: Английский