Journal
TETRAHEDRON LETTERS
Volume 44, Issue 16, Pages 3397-3400Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(03)00570-7
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Stereospecific lithiation of N-alpha-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 alpha-methyl analogue of kainic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.
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