Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

Article abstract of DOI:10.1016/S0040-4039(99)01765-7

Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.