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)
Pages (from-to)	1041-1044
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201800728
State	Published - Jul 2019

Keywords

anionic cascade
annulation
asymmetry
kainic acid
sulfonamide

ASJC Scopus subject areas

Organic Chemistry

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

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.",

keywords = "anionic cascade, annulation, asymmetry, kainic acid, sulfonamide",

author = "Isaac Chogii and Pradipta Das and Njardarson, {Jon T.}",

note = "Funding Information: Financial support for this work was provided by The National Science Foundation (CHE-1565500). We thank Dr. Sue Roberts for assitance with X-ray crystallography data acquisition and analysis. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/ajoc.201800728",

language = "English (US)",

volume = "8",

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T2 - Unexpected Sulfinamide-Directed Conjugate Addition Results

AU - Chogii, Isaac

AU - Das, Pradipta

AU - Njardarson, Jon T.

N1 - Funding Information: Financial support for this work was provided by The National Science Foundation (CHE-1565500). We thank Dr. Sue Roberts for assitance with X-ray crystallography data acquisition and analysis. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/7

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N2 - 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.

AB - 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.

KW - anionic cascade

KW - annulation

KW - asymmetry

KW - kainic acid

KW - sulfonamide

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

Abstract

Keywords

ASJC Scopus subject areas

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