Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides: Formal synthesis of (-)-kainic acid

Jonathan Clayden; Christel J. Menet; Darren J. Mansfield

doi:10.1039/b109188c

Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides: Formal synthesis of (-)-kainic acid

Jonathan Clayden, Christel J. Menet, Darren J. Mansfield

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

Abstract

Chiral lithium amides deprotonate N-benzyl benzamides enantioselectively, initiating an asymmetric dearomatising cyclisation to enantiomerically enriched isoindolinones.

Original language	English
Pages (from-to)	38-39
Number of pages	1
Journal	Chemical Communications
Issue number	1
DOIs	https://doi.org/10.1039/b109188c
Publication status	Published - 7 Jan 2002

Keywords

Asymmetric synthesis and induction; Cyclization; Lithiation; Stereochemistry (asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid); Amino acids Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid); Deprotonation (asym.; asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid)

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title = "Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides: Formal synthesis of (-)-kainic acid",

abstract = "Chiral lithium amides deprotonate N-benzyl benzamides enantioselectively, initiating an asymmetric dearomatising cyclisation to enantiomerically enriched isoindolinones.",

keywords = "Asymmetric synthesis and induction; Cyclization; Lithiation; Stereochemistry (asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid); Amino acids Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid); Deprotonation (asym.; asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid)",

author = "Jonathan Clayden and Menet, {Christel J.} and Mansfield, {Darren J.}",

year = "2002",

month = jan,

day = "7",

doi = "10.1039/b109188c",

language = "English",

pages = "38--39",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "1",

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T1 - Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides: Formal synthesis of (-)-kainic acid

AU - Clayden, Jonathan

AU - Menet, Christel J.

AU - Mansfield, Darren J.

PY - 2002/1/7

Y1 - 2002/1/7

N2 - Chiral lithium amides deprotonate N-benzyl benzamides enantioselectively, initiating an asymmetric dearomatising cyclisation to enantiomerically enriched isoindolinones.

AB - Chiral lithium amides deprotonate N-benzyl benzamides enantioselectively, initiating an asymmetric dearomatising cyclisation to enantiomerically enriched isoindolinones.

KW - Asymmetric synthesis and induction; Cyclization; Lithiation; Stereochemistry (asym. deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides in the formal synthesis of (-)-kainic acid); Amino acids Role: RCT (Reactant

U2 - 10.1039/b109188c

DO - 10.1039/b109188c

M3 - Article

SN - 1359-7345

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JO - Chemical Communications

JF - Chemical Communications

IS - 1

ER -

Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides: Formal synthesis of (-)-kainic acid

Abstract

Keywords

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