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Issue 11, 2017
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Diastereoselective building up polycyclic tetrahydrofurans via tandem annulation of 1,n-enynes with aliphatic acids

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Abstract

A silver-catalyzed tandem annulation of aniline-linked 1,7-enynes with aliphatic acids has been reported. This synergistic tandem annulations allow the straightforward and efficient building up various highly diastereoselective polycyclic tetrahydrofurans. Primary and secondary acids undergo decarboxylation/cascade radical addition/α-C(sp3)–H cleavage/cycloalkylation/O-trapping to generate oxygenous [6.6.6.5] fused products. While tertiary acids undergo decarboxylation/cascade radcial addition/β-C(sp3)–H cleavage/O-trapping to give oxygenous [6.6.6.6] fused products.

Graphical abstract: Diastereoselective building up polycyclic tetrahydrofurans via tandem annulation of 1,n-enynes with aliphatic acids

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Article information


Submitted
28 Jun 2017
Accepted
24 Jul 2017
First published
24 Jul 2017

Org. Chem. Front., 2017,4, 2147-2152
Article type
Research Article

Diastereoselective building up polycyclic tetrahydrofurans via tandem annulation of 1,n-enynes with aliphatic acids

L. Lv, S. Lu, Y. Chen and Z. Li, Org. Chem. Front., 2017, 4, 2147
DOI: 10.1039/C7QO00527J

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