Enantioselective Synthesis of 3-Arylindan-1-ones via Intramolecular C-H Insertion Reactions of α-Diazo-β-Ketoesters Catalyzed by Chiral Dirhodium(II) Carboxylates

摘要

A new, catalytic enantioselective route to 3-arylindan-1-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 α-diazo-β-ketoesters as a key step. Dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, proved to be the catalyst of choice for this process, providing enantioselectivities of up to 72% ee.