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An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones.
- Source :
- Dalton Transactions: An International Journal of Inorganic Chemistry; 6/21/2020, Vol. 49 Issue 23, p7959-7967, 9p
- Publication Year :
- 2020
-
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, (S<subscript>A</subscript>,R<subscript>P</subscript>,SS)-7a and (S<subscript>A</subscript>,R<subscript>P</subscript>,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 (S<subscript>A</subscript>,R<subscript>P</subscript>,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 (S<subscript>A</subscript>,R<subscript>P</subscript>,RR)-7b′ afforded an enantioselective catalyst for the preparation of chiral alcohols with moderate to good yields and a broad functional group tolerance. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14779226
- Volume :
- 49
- Issue :
- 23
- Database :
- Complementary Index
- Journal :
- Dalton Transactions: An International Journal of Inorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 143805616
- Full Text :
- https://doi.org/10.1039/d0dt01204a