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Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring via vinylogous C–N bond formation†
Sadagopan Raghavan,Anil Ravi
Organic & Biomolecular Chemistry Pub Date : 10/07/2016 00:00:00 , DOI:10.1039/C6OB01966H
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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