Cation-n control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams

Michal Szostak, Lei Yao, Jeffrey Aubé

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The regiochemistry of the intramolecular Schmidt reaction of 2-azidoalkylketones is controlled by placing a thioether substituent at the position adjacent to the ketone to provide access to a family of unsubstituted medium bridged twisted amides. This outcome Is ascribed to the presence of stabilizing through-space interactions between the diazonium cation and the n electrons on heteroatom and does not require a locked conformation of the ketone.

Original languageEnglish (US)
Pages (from-to)4386-4389
Number of pages4
JournalOrganic letters
Volume11
Issue number19
DOIs
StatePublished - Oct 1 2009
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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