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 journal › Article

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

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sulfoxide
Addition reactions
Nitrogen
Atoms
pyrroline

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efforts Toward a Unified Kainoid Family Synthesis Approach : Unexpected Sulfinamide-Directed Conjugate Addition Results. / Chogii, Isaac; Das, Pradipta; Njardarson, Jon T.

In: Asian Journal of Organic Chemistry, 01.01.2019.

Research output: Contribution to journal › Article

Chogii, I, Das, P & Njardarson, JT 2019, 'Efforts Toward a Unified Kainoid Family Synthesis Approach: Unexpected Sulfinamide-Directed Conjugate Addition Results', Asian Journal of Organic Chemistry. https://doi.org/10.1002/ajoc.201800728
Chogii I, Das P, Njardarson JT. Efforts Toward a Unified Kainoid Family Synthesis Approach: Unexpected Sulfinamide-Directed Conjugate Addition Results. Asian Journal of Organic Chemistry. 2019 Jan 1. https://doi.org/10.1002/ajoc.201800728
Chogii, Isaac ; Das, Pradipta ; Njardarson, Jon T. / Efforts Toward a Unified Kainoid Family Synthesis Approach : Unexpected Sulfinamide-Directed Conjugate Addition Results. In: Asian Journal of Organic Chemistry. 2019.
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