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  • Title: Enantioselective synthesis of cyclobutanes via sequential Rh-catalyzed bicyclobutanation/Cu-catalyzed homoconjugate addition.
    Author: Panish R, Chintala SR, Boruta DT, Fang Y, Taylor MT, Fox JM.
    Journal: J Am Chem Soc; 2013 Jun 26; 135(25):9283-6. PubMed ID: 23758288.
    Abstract:
    Enantiomerically enriched cyclobutanes are constructed by a three-component process in which t-butyl (E)-2-diazo-5-arylpent-4-enoates are treated with Rh2(S-NTTL)4 to provide enantiomerically enriched bicyclobutanes, which can subsequently engage in homoconjugate addition/enolate trapping sequence to give densely functionalized cyclobutanes with high diastereoselectivity. This three-component, two-catalyst procedure can be carried out in a single flask. Rh2(S-NTTL)4-catalyzed reaction of t-butyl (Z)-2-diazo-5-phenylpent-4-enoate gives the Büchner cyclization product in excellent enantioselectivity.
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