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

Isaac Chogii; Pradipta Das; Jon T Njardarson

doi:10.1002/ajoc.201800728

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

Isaac Chogii, Pradipta Das, Jon T Njardarson

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Journal	Asian Journal of Organic Chemistry
DOIs	https://doi.org/10.1002/ajoc.201800728
State	Published - Jan 1 2019

Keywords

anionic cascade
annulation
asymmetry
kainic acid
sulfonamide

ASJC Scopus subject areas

Organic Chemistry

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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.",

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AU - Das, Pradipta

AU - Njardarson, Jon T

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KW - annulation

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