Journal
DALTON TRANSACTIONS
Volume 49, Issue 23, Pages 7959-7967Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0dt01204a
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Funding
- Natural Science Foundation of China [21772021]
- Shanghai Rising-Star Program [16QA1400100]
- Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning [TP2014035]
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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 potassiumtert-butoxide, (S-A,R-P,SS)-7aand (S-A,R-P,SS)-7bare active but nonenantioselective catalysts for the transfer hydrogenation of acetophenone and alpha,beta-unsaturated aldehydes at room temperature in isopropanol. A maximum turnover number of 14480 was observed for (S-A,R-P,SS)-7ain 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 (S-A,R-P,RR)-7b ' afforded an enantioselective catalyst for the preparation of chiral alcohols with moderate to good yields and a broad functional group tolerance.
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