Issue 12, 2015

C–H insertions in oxidative gold catalysis: synthesis of polycyclic 2H-pyran-3(6H)-ones via a relay strategy

Abstract

An expedient synthesis of bicyclic/polycyclic 2H-pyran-3(6H)-ones is realized in a cascade cyclization triggered by oxidative gold catalysis and terminated by streamlining C–H insertions. In this reaction, an α-oxo gold carbene intermediate, initially formed upon gold-catalyzed oxidation of alkynes, could be trapped by a tethered C–C triple bond, thereby resulting in the formation of a putative vinyl cation intermediate. This intermediate of high electrophilicity is proposed to be responsible for intramolecular C–H insertions, the mostly concerted nature of which is established by the reactions of chiral substrates. The reaction provides a rapid approach to the construction of functionalized polycyclic systems from easily accessible bispropargyl ethers and with minimal structural prefunctionalization.

Graphical abstract: C–H insertions in oxidative gold catalysis: synthesis of polycyclic 2H-pyran-3(6H)-ones via a relay strategy

Supplementary files

Article information

Article type
Research Article
Submitted
07 ⴽⵜⵓ 2015
Accepted
13 ⴽⵜⵓ 2015
First published
14 ⴽⵜⵓ 2015

Org. Chem. Front., 2015,2, 1556-1560

Author version available

C–H insertions in oxidative gold catalysis: synthesis of polycyclic 2H-pyran-3(6H)-ones via a relay strategy

Z. Zheng and L. Zhang, Org. Chem. Front., 2015, 2, 1556 DOI: 10.1039/C5QO00308C

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