σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines

Feng Hu, Pradeep Nareddy, Roger Lalancette, Frank Jordan, Michal Szostak

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

A rare example of highly selective σ N-C bond difunctionalization in bridged twisted lactams through N-C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (“sew-and-cut”) to access functionalized isoquinoline ring systems directly with high atom economy. C-H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in this unusual σ N-C amide difunctionalization are described.

Original languageEnglish (US)
Pages (from-to)2386-2389
Number of pages4
JournalOrganic letters
Volume19
Issue number9
DOIs
StatePublished - May 5 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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