Highly efficient ruthenium-catalyzed asymmetric hydrogenation of N-heteroaryl vinyl ethers?

Organic Chemistry Frontiers Pub Date: 2022-04-16 DOI: 10.1039/D2QO00448H

Abstract

A highly efficient N-heteroaryl-directed Ru-catalyzed asymmetric hydrogenation of α,α-disubstituted vinyl ethers was successfully achieved by using the commercially available ligand (R/S)-RuCl[(p-cymene)(BINAP)]Cl. Hundred-gram scale-up of 6a was successfully completed with a consistent ee value and good yield. Various types of N-heteroaryl-substituted vinyl ethers could be hydrogenated with good to excellent enantioselectivities, providing an attractive method for the synthesis of pharmaceutically active heteroaryl compounds containing chiral ether units.

Graphical abstract: Highly efficient ruthenium-catalyzed asymmetric hydrogenation of N-heteroaryl vinyl ethers
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