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Issue 43, 2016
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Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring via vinylogous C–N bond formation

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Abstract

The synthesis of crinane is disclosed via intramolecular C–N bond formation by the displacement of an allylic sulfoxonium salt. The allylic sulfide precursor was synthesized by a ring-closing metathesis reaction. The quaternary carbon stereocenter was created by alkylation of a benzylic cyanide. The allyl sulfide 14 was prepared by adding vinylmagnesium bromide to an α-chlorosulfide.

Graphical abstract: Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring via vinylogous C–N bond formation

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Article information


Submitted
06 Sep 2016
Accepted
07 Oct 2016
First published
07 Oct 2016

Org. Biomol. Chem., 2016,14, 10222-10229
Article type
Paper

Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring via vinylogous C–N bond formation

S. Raghavan and A. Ravi, Org. Biomol. Chem., 2016, 14, 10222
DOI: 10.1039/C6OB01966H

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