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

Research output: Contribution to journalArticle (Academic Journal)

33 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 languageEnglish
Pages (from-to)3397-3400
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number16
Early online date28 Mar 2003
DOIs
Publication statusPublished - 14 Apr 2003

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