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Issue 8, 2018
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Efficient access to chiral benzo[c]chromenes via asymmetric transfer hydrogenation of ketals

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Abstract

A highly enantioselective synthetic method to access chiral α-substituted 6H-benzo[c]chromenes through chiral imidodiphosphoric acid-catalyzed asymmetric transfer hydrogenation of the corresponding ketals has been established. The substituent patterns at the α-position proved to be unsusceptible to the asymmetric catalysis system, with diverse hybrid substituents including aryl and vinyl, alkynyl, and alkyl moieties that were well tolerated. In addition, the generality of the method was further demonstrated by application to 1H-isochromene-based ketals, offering chiral α-aryl and -alkyl 1H-isochromenes in excellent ee.

Graphical abstract: Efficient access to chiral benzo[c]chromenes via asymmetric transfer hydrogenation of ketals

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Supplementary files

Article information


Submitted
28 Jan 2018
Accepted
26 Feb 2018
First published
08 Mar 2018

Org. Chem. Front., 2018,5, 1280-1283
Article type
Research Article

Efficient access to chiral benzo[c]chromenes via asymmetric transfer hydrogenation of ketals

Y. Li, M. Wan, S. Sun, Z. Fu, H. Huang and L. Liu, Org. Chem. Front., 2018, 5, 1280
DOI: 10.1039/C8QO00096D

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