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Catalytic enantioselective cross-dehydrogenative coupling of 3,6-dihydro-2H-pyrans with aldehydes

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Abstract

The existing catalytic asymmetric synthesis of enantiopure α-substituted 3,6-dihydro-2H-pyrans and tetrahydropyrans predominantly relies on the oxygen heterocycle construction strategy involving enantioselective cyclization of pre-functionalized olefin substrates. Given the easy availability of the cyclic ether skeleton, we disclosed the first catalytic asymmetric cross-dehydrogenative coupling of 3,6-dihydro-2H-pyrans and aldehydes. The reaction exhibits excellent enantioselectivity, good functional group tolerance, and wide compatibility of diverse 3,6-dihydro-2H-pyran and aldehyde components, thus providing a practical and economical method for enantiopure α-substituted 3,6-dihydro-2H-pyran synthesis.

Graphical abstract: Catalytic enantioselective cross-dehydrogenative coupling of 3,6-dihydro-2H-pyrans with aldehydes

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Publication details

The article was received on 25 Jan 2019, accepted on 07 Mar 2019 and first published on 20 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00123A
Citation: Org. Chem. Front., 2019, Advance Article

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    Catalytic enantioselective cross-dehydrogenative coupling of 3,6-dihydro-2H-pyrans with aldehydes

    X. Xin, X. Pan, Z. Meng, X. Liu and L. Liu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00123A

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