Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide

Jonathan Clayden; Faye E. Knowles; Christel J. Menet

doi:10.1016/S0040-4039(03)00570-7

Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide

Jonathan Clayden^*, Faye E. Knowles, Christel J. Menet

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

34 Citations (Scopus)

Abstract

Stereospecific lithiation of N-α-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the α-methyl analogue of kainic acid.

Original language	English
Pages (from-to)	3397-3400
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	16
Early online date	28 Mar 2003
DOIs	https://doi.org/10.1016/S0040-4039(03)00570-7
Publication status	Published - 14 Apr 2003

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title = "Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide",

abstract = "Stereospecific lithiation of N-α-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the α-methyl analogue of kainic acid.",

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T1 - Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide

AU - Clayden, Jonathan

AU - Knowles, Faye E.

AU - Menet, Christel J.

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Y1 - 2003/4/14

N2 - Stereospecific lithiation of N-α-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the α-methyl analogue of kainic acid.

AB - Stereospecific lithiation of N-α-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the α-methyl analogue of kainic acid.

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U2 - 10.1016/S0040-4039(03)00570-7

DO - 10.1016/S0040-4039(03)00570-7

M3 - Article (Academic Journal)

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ER -

Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide

Abstract

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