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Issue 2, 2017
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Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C–H activation

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Abstract

The diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(III) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the O-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[c]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules.

Graphical abstract: Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C–H activation

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Publication details

The article was received on 13 Jun 2016, accepted on 13 Sep 2016 and first published on 23 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC02587K
Citation: Chem. Sci., 2017,8, 1015-1020
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    Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C–H activation

    N. Semakul, K. E. Jackson, R. S. Paton and T. Rovis, Chem. Sci., 2017, 8, 1015
    DOI: 10.1039/C6SC02587K

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