Modular access to substituted azocanes via a rhodium-catalyzed cycloaddition-fragmentation strategy

Megan H. Shaw, Rosemary A. Croft, William G. Whittingham, John F. Bower

Research output: Contribution to journalArticle (Academic Journal)peer-review

49 Citations (Scopus)
331 Downloads (Pure)

Abstract

A short entry to substituted azocanes by a Rh-catalyzed cycloadditio −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.
Original languageEnglish
Pages (from-to)8054-8057
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number25
DOIs
Publication statusPublished - 19 Jun 2015

Structured keywords

  • BCS and TECS CDTs

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