Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemsitry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China.
Chem Soc Rev. 2015 Feb 7;44(3):677-98. doi: 10.1039/c4cs00304g.
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.
均相金催化环丙烷化反应因其丰富的化学性质和迷人的反应性而成为有机合成中的一种强大方法。这种蓬勃发展的策略以其温和的条件、良好的选择性和高效率为突出特点，为传统金属催化环丙烷化提供了互补性和正交性。本文综述了根据碳烯前体的类型对金催化环丙烷化反应的最新进展。除了常用的重氮化合物外，目前的方法还可以使易得的烯炔、炔丙酯、环丙烯、环庚三烯、炔烃和锍叶立德等作为金碳烯化学领域更安全的替代物。同时，这些反应允许快速构建分子复杂性，包括合成有用的复杂环状、杂环和多环骨架。金配合物的新反应性与催化环丙烷化的能力相结合，可能为新反应的设计带来无数机会。此外，通过选择的天然和具有生物意义的产物的全合成以及具有挑战性的靶分子的对映选择性形成，也说明了这些优越方法的合成实用性。
