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Paper | Special issue | Vol 61, No. 1, 2003, pp.391-401
Published online, 6th October, 2003
DOI: 10.3987/COM-03-S55
Synthesis and Evaluation of Novel Dirhodium(II) Carboxylate Catalysts with Atropisomeric Biaryl Backbone

Ken Hikichi, Shinji Kitagaki, Masahiro Anada, Seiichi Nakamura, Makoto Nakajima, Motoo Shiro, and Shunichi Hashimoto*

*Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Hokkaido

Abstract

Three new dirhodium(II) carboxylate catalysts containing an axially dissymmetric biphenyl or binaphthyl skeleton have been synthesized and characterized. The X-Ray structure of the dirhodium(II) complex incorporating (R)-2'-methoxycarbonyl-6,6'-dimethyl-[1,1'-biphenyl]-2-carboxylate as bridging ligands demonstrates that the four carboxylate ligands are arranged in a C2-symmetry-like conformation. These catalysts have been shown to provide a reasonable level of asymmetric induction in intramolecular C—H insertion of α-methoxycarbonyl-α-diazoacetamide.