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Issue 36, 2016
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Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite–urea bifunctional catalysts

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Abstract

Chiral phosphite–urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

Graphical abstract: Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite–urea bifunctional catalysts

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Publication details

The article was received on 10 Jan 2016, accepted on 18 Mar 2016 and first published on 18 Mar 2016


Article type: Communication
DOI: 10.1039/C6CC00229C
Chem. Commun., 2016,52, 6068-6071
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    Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite–urea bifunctional catalysts

    Y. Sawamura, Y. Ogura, H. Nakatsuji, A. Sakakura and K. Ishihara, Chem. Commun., 2016, 52, 6068
    DOI: 10.1039/C6CC00229C

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