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Issue 24, 2010
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Desymmetrization of 7-dimethylphenylsilylcycloheptatriene. Towards the synthesis of new aminocycloheptitols

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Abstract

Desymmetrization of 7-silylcycloheptatriene through consecutive dihydroxylation and acyl-nitroso cycloaddition of the resulting diene moiety is described. Dihydroxylation occurred anti relative to the resident silicon group in line with previous observations made in the cyclohexadiene series. In contrast, the subsequent acyl-nitroso cycloaddition occurred with poor regiocontrol but good level of diastereocontrol syn to the bulky silyl substituent. The resulting cycloadducts were then elaborated further to provide a straightforward entry toward aminocycloheptitols in ten steps from commercially available tropylium salts.

Graphical abstract: Desymmetrization of 7-dimethylphenylsilylcycloheptatriene. Towards the synthesis of new aminocycloheptitols

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Publication details

The article was received on 30 Jul 2010, accepted on 07 Sep 2010 and first published on 13 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00521E
Citation: Org. Biomol. Chem., 2010,8, 5628-5634
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    Desymmetrization of 7-dimethylphenylsilylcycloheptatriene. Towards the synthesis of new aminocycloheptitols

    E. Girard, V. Desvergnes, C. Tarnus and Y. Landais, Org. Biomol. Chem., 2010, 8, 5628
    DOI: 10.1039/C0OB00521E

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