Modular Access to Substituted Azocanes Via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2015 Jun 20

PMID 26090897

Citations 19

Authors

Megan H Shaw

Rosemary A Croft

William G Whittingham

John F Bower

Affiliations

Soon will be listed here.

Abstract

A short entry to substituted azocanes by a Rh-catalyzed cycloaddition-fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.

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