Enantioselective Synthesis of Planar-Chiral Metacyclophanes through Rhodium-Catalyzed Alkyne Cyclotrimerization

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J. Am. Chem. Soc., 129 (6), 1522 -1523, 2007. 10.1021/ja0679127 S0002-7863(06)07912-1
Web Release Date: January 18, 2007

Enantioselective Synthesis of Planar-Chiral Metacyclophanes through Rhodium-Catalyzed Alkyne Cyclotrimerization

Ken Tanaka,* Hiromi Sagae, Kazuki Toyoda, Keiichi Noguchi, and Masao Hirano

Department of Applied Chemistry, Graduate School of Engineering, and Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan

tanaka-k@cc.tuat.ac.jp

Received November 6, 2006

Abstract:

We have achieved the first catalytic enantioselective synthesis of planar-chiral metacyclophanes by means of cationic rhodium(I)/(R)-H₈-BINAP complex-catalyzed alkyne cyclotrimerization. This reaction represents a versatile new method for the preparation of planar-chiral [7]-[10]metacyclophanes.

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