ENANTIOSELECTIVE SYNTHESIS OF 3-ARYLINDAN-l-ONES VIA INTRAMOLECULAR C-H INSERTION REACTIONS OF alphalpha-DIAZO-betalpha-KETOESTERS CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXYLATESt

摘要

A new, catalytic enantioselective route to 3-arylindan-l-ones, versatile intermediates for the synthesis of a number of bioactive and pharmaceutically interesting molecules, was developed by exploiting the chiral dirhodium(II) complex-catalyzed intramolecular C-H insertion reaction of alphalpha-diazo-betalpha-ketoesters as a key step. Dirhodium(II) tetrakis[Ar-phthaloyl-(5)-tert-leucinate], Rh_2(S-PTTL)_4, proved to be the catalyst of choice for this process, providing enantioselectivities of up to 72% ee.