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Issue 3, 2015
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Gold-catalyzed cyclopropanation reactions using a carbenoid precursor toolbox

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Homogeneous gold-catalyzed cyclopropanation has emerged as a powerful method in organic synthesis due to its rich chemistry and fascinating reactivity. This thriving strategy is remarkable for its mild conditions, good selectivity, and high efficiency, which provides complementarity and orthogonality to traditional metal-catalyzed cyclopropanation. This review summarizes recent advances in gold-catalyzed cyclopropanation divided by the type of carbenoid precursors. Besides the commonly used diazo compounds, current approaches enable readily available enynes, propargyl esters, cyclopropenes, cycloheptatrienes, alkynes, and sulfonium ylides as safer surrogates in the realm of gold carbenoid chemistry. Meanwhile, these reactions allow for the rapid building of molecular complexity including synthetically useful and intricate cyclic, heterocyclic, and polycyclic skeletons. The combination of the new reactivity of gold complexes with their capability to catalyze cyclopropanations may lead to myriad opportunities for the design of new reactions. Furthermore, the synthetic utilities of such superior methods have also been illustrated by the total syntheses of selected natural and biologically interesting products and the asymmetric formation of challenging target molecules.

Graphical abstract: Gold-catalyzed cyclopropanation reactions using a carbenoid precursor toolbox

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Publication details

The article was received on 11 Sep 2014 and first published on 18 Dec 2014

Article type: Review Article
DOI: 10.1039/C4CS00304G
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Chem. Soc. Rev., 2015,44, 677-698

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    Gold-catalyzed cyclopropanation reactions using a carbenoid precursor toolbox

    D. Qian and J. Zhang, Chem. Soc. Rev., 2015, 44, 677
    DOI: 10.1039/C4CS00304G

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