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Issue 19, 2018
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Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution

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Abstract

A new class of tunable heterophosphole dimeric ligands have been designed and synthesized. These ligands have enabled the first examples of Cu-catalyzed hydrogenation of 2-substituted-1-tetralones and related heteroaryl ketones via dynamic kinetic resolution, simultaneously creating two contiguous stereogenic centers with up to >99 : 1 dr and 98 : 2 er. The ligand-Cu complexes were isolated and characterized by single crystal X-ray, and DFT calculations revealed a novel heteroligated dimeric copper hydride transition state.

Graphical abstract: Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution

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Supplementary files

Article information


Submitted
26 Jan 2018
Accepted
19 Apr 2018
First published
23 Apr 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 4505-4510
Article type
Edge Article

Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution

Olga V. Zatolochnaya, S. Rodríguez, Y. Zhang, K. S. Lao, S. Tcyrulnikov, G. Li, X. Wang, B. Qu, S. Biswas, H. P. R. Mangunuru, D. Rivalti, J. D. Sieber, J. Desrosiers, J. C. Leung, N. Grinberg, H. Lee, N. Haddad, N. K. Yee, J. J. Song, M. C. Kozlowski and C. H. Senanayake, Chem. Sci., 2018, 9, 4505
DOI: 10.1039/C8SC00434J

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