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Issue 9, 2019
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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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Article information


Submitted
25 Jan 2019
Accepted
07 Mar 2019
First published
20 Mar 2019

Org. Chem. Front., 2019,6, 1448-1452
Article type
Research Article

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, 6, 1448
DOI: 10.1039/C9QO00123A

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