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Issue 23, 2020
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An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones

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Abstract

We report the design of a new iron catalyst for the asymmetric transfer hydrogenation of ketones. This type of iron catalyst combines the structural characteristics of the Noyori hydrogenation catalyst (an axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl fragment and the metal–ligand bifunctional motif) and an ene(amido) group that can activate the iron center. After activation by 8 equivalents of potassium tert-butoxide, (SA,RP,SS)-7a and (SA,RP,SS)-7b are active but nonenantioselective catalysts for the transfer hydrogenation of acetophenone and α,β-unsaturated aldehydes at room temperature in isopropanol. A maximum turnover number of 14480 was observed for (SA,RP,SS)-7a in the reduction of acetophenone. The right combination of the stereochemistry of the axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl group and the carbon-centered chiral amine-imine moiety in (SA,RP,RR)-7b′ afforded an enantioselective catalyst for the preparation of chiral alcohols with moderate to good yields and a broad functional group tolerance.

Graphical abstract: An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones

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Article information


Submitted
01 Apr 2020
Accepted
14 May 2020
First published
14 May 2020

Dalton Trans., 2020,49, 7959-7967
Article type
Paper

An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones

S. Huo, Q. Wang and W. Zuo, Dalton Trans., 2020, 49, 7959
DOI: 10.1039/D0DT01204A

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