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RhI-Catalyzed Regio- and Stereospecific Carbonylation of 1-(1-Alkynyl)cyclopropyl Ketones: A Modular Entry to Highly Substituted 5,6-Dihydrocyclopenta[c]furan-4-ones

Authors

  • Yanqing Zhang,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-3213
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  • Zuliang Chen,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-3213
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  • Yuanjing Xiao Dr.,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-3213
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  • Junliang Zhang Prof. Dr.

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-3213
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (P.R. China)
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Abstract

Efficient route: A novel RhI-catalyzed regio- and stereospecific carbonylation reaction of (1-alkynyl)cyclopropyl ketones by selective activation of a carbon[BOND]carbon σ bond of the cyclopropane ring was demonstrated (see scheme). This method provides a general, efficient, stereoselective route to synthesise 1,3,5-trisubstituted and 1,3,5,6-tetrasubstituted 5,6-dihydrocyclopenta[c]furan-4-one with convertible functional groups.

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