Issue 43, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Sep 2016
Accepted
07 Oct 2016
First published
07 Oct 2016

Org. Biomol. Chem., 2016,14, 10222-10229

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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