Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Jonathan Clayden; Christel J. Menet; Kirill Tchabanenko

doi:10.1016/S0040-4020(02)00379-4

Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Jonathan Clayden, Christel J. Menet, Kirill Tchabanenko

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

Abstract

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	4727-4733
Number of pages	6
Journal	Tetrahedron
Volume	58
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4020(02)00379-4
Publication status	Published - 3 Jun 2002

Keywords

Cyclization
Kainic acid
Lithium amide
Organolithium
Stereoselective

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10.1016/S0040-4020(02)00379-4

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title = "Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization",

abstract = "Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "Cyclization, Kainic acid, Lithium amide, Organolithium, Stereoselective",

author = "Jonathan Clayden and Menet, {Christel J.} and Kirill Tchabanenko",

year = "2002",

month = jun,

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doi = "10.1016/S0040-4020(02)00379-4",

language = "English",

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TY - JOUR

T1 - Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

AU - Clayden, Jonathan

AU - Menet, Christel J.

AU - Tchabanenko, Kirill

PY - 2002/6/3

Y1 - 2002/6/3

N2 - Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid. © 2002 Elsevier Science Ltd. All rights reserved.

AB - Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Cyclization

KW - Kainic acid

KW - Lithium amide

KW - Organolithium

KW - Stereoselective

U2 - 10.1016/S0040-4020(02)00379-4

DO - 10.1016/S0040-4020(02)00379-4

M3 - Article

SN - 0040-4020

VL - 58

SP - 4727

EP - 4733

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Abstract

Keywords

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