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  • Title: Diastereoselective [4 + 1] cycloaddition of alkenyl propargyl acetates with CO catalyzed by [RhCl(CO)2]2.
    Author: Chen W, Tay JH, Yu XQ, Pu L.
    Journal: J Org Chem; 2012 Jul 20; 77(14):6215-22. PubMed ID: 22725622.
    Abstract:
    A class of alkenyl propargyl acetates, RCH(OAc)C≡CC(CH(3))═CH(2) (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents, up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.
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