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Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds

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Abstract

A highly enantioselective hydrogenation of exocyclic α,β-unsaturated carbonyl compounds catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) has been developed, giving the corresponding α-chiral cyclic lactones, lactams and ketones with high yields and excellent enantioselectivities (up to 99% yield and 99% ee). Remarkably, the hydrogen bond between the substrate and the catalyst plays a critical role in this transformation. The synthetic utility of this protocol has been demonstrated by efficient synthesis of chiral 3-(4-fluorobenzyl)piperidine, a key chiral fragment of bioactive molecules.

Graphical abstract: Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds

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Article information


Submitted
27 Nov 2019
Accepted
02 Jan 2020
First published
15 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds

J. Yang, X. Li, C. You, S. Li, Y. Guan, H. Lv and X. Zhang, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02536G

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