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Note | Special issue | Vol 70, No. 1, 2006, pp.635-646
Published online, 17th November, 2006
DOI: 10.3987/COM-06-S(W)58
Enantioselective Synthesis of 3-Arylindan-1-ones via Intramolecular C-H Insertion Reactions of α-Diazo-β-Ketoesters Catalyzed by Chiral Dirhodium(II) Carboxylates

Yoshihiro Natori, Masahiro Anada, Seiichi Nakamura, Hisanori Nambu, and Shunichi Hashimoto*

*Laboratory of Synthetic and Industrial Chemistry, Graduate School of Life Science, Division of Life Science, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

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.