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.
|Number of pages||4|
|Early online date||28 Mar 2003|
|Publication status||Published - 14 Apr 2003|