Issue 4, 2022

Asymmetric hydrogenation and transfer hydrogenation in the enantioselective synthesis of flavonoids

Abstract

Asymmetric hydrogenation (AH) and asymmetric transfer hydrogenation (ATH) are versatile synthetic methodologies widely employed in the preparation of chiral compounds. In this review, we explore the applications of AH and ATH in the total synthesis of natural flavonoids and their analogues, highlighting the limitations and opportunities in the field. Regarding AH, the hydrogenation of the C[double bond, length as m-dash]C bond of chromenes and cinnamic acid derivatives leads to isoflavans, flavans, flavanones and homoisoflavones with excellent enantioselectivity. Analogously, the ATH of C[double bond, length as m-dash]O and C[double bond, length as m-dash]C/C[double bond, length as m-dash]O bonds results in enantioenriched alcohols, which upon oxidation, deoxygenation or cyclization allow the synthesis of a myriad of flavonoids, isoflavonoids and homoisoflavonoids with excellent yields and ee values.

Graphical abstract: Asymmetric hydrogenation and transfer hydrogenation in the enantioselective synthesis of flavonoids

Article information

Article type
Review Article
Submitted
07 Oct 2021
Accepted
30 Nov 2021
First published
30 Nov 2021

Org. Chem. Front., 2022,9, 1165-1194

Asymmetric hydrogenation and transfer hydrogenation in the enantioselective synthesis of flavonoids

G. S. Caleffi, F. C. Demidoff, C. Nájera and P. R. R. Costa, Org. Chem. Front., 2022, 9, 1165 DOI: 10.1039/D1QO01503F

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