Efforts Toward a Unified Kainoid Family Synthesis Approach: Unexpected Sulfinamide-Directed Conjugate Addition Results

Isaac Chogii, Pradipta Das, Jon T Njardarson

Research output: Contribution to journalArticle

Abstract

A short asymmetric synthesis of an all-syn and all-trans kainoid core is reported. The synthetic route relies on the application of a new asymmetric [3+2] annulation reaction followed by a conjugate addition reaction to install this kainoid's three stereocenters. A surprising intramolecular conjugate addition enabled by the chiral tert-butylsulfinyl group residing on the 3-pyrroline nitrogen atom surpassed its expected role as a steric spectator. Efforts to outcompete intramolecular 1,4-addition by further oxidizing the sulfoxide, or use of additives, and advancement of the all-syn addition product to the requisite kainoid common core are detailed.

Original languageEnglish (US)
JournalAsian Journal of Organic Chemistry
DOIs
StatePublished - Jan 1 2019

Keywords

  • anionic cascade
  • annulation
  • asymmetry
  • kainic acid
  • sulfonamide

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Efforts Toward a Unified Kainoid Family Synthesis Approach: Unexpected Sulfinamide-Directed Conjugate Addition Results'. Together they form a unique fingerprint.

  • Cite this