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A New Type of Catalytic Tandem 1,4-Addition-Aldol Reaction Which Proceeds through an (Oxa-π-allyl)rhodium Intermediate

Kazuhiro Yoshida, Masamichi Ogasawara, and Tamio Hayashi*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: thayashikuchem.kyoto-u.ac.jp

K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc., 2002, 124, 10984-10985.

DOI: 10.1021/ja0271025 (free Supporting Information)


Abstract

The Rh-catalyzed reaction of 9-aryl-9-borabicyclo[3.3.1]nonanes with α,β-unsaturated ketones and aldehydes gave high yields of tandem 1,4-addition-aldol reaction products with high syn selectivity. The mechanism is discussed.

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Key Words

Hydroxy ketones, Arylation


ID: J48-Y2002-1270