Gold-catalyzed cyclopropanation reactions using a carbenoid precursor toolbox. 2015

Deyun Qian, and Junliang Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemsitry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. jlzhang@chem.ecnu.edu.cn.

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.

UI MeSH Term Description Entries

Related Publications

Deyun Qian, and Junliang Zhang
March 2004, Chemical Society reviews,
Deyun Qian, and Junliang Zhang
January 2019, Beilstein journal of organic chemistry,
Deyun Qian, and Junliang Zhang
December 2005, Journal of the American Chemical Society,
Deyun Qian, and Junliang Zhang
August 2004, The Journal of organic chemistry,
Deyun Qian, and Junliang Zhang
November 2014, Angewandte Chemie (International ed. in English),
Deyun Qian, and Junliang Zhang
January 2007, Chemistry (Weinheim an der Bergstrasse, Germany),
Deyun Qian, and Junliang Zhang
February 2006, Chemistry (Weinheim an der Bergstrasse, Germany),
Deyun Qian, and Junliang Zhang
May 2006, Organic letters,
Deyun Qian, and Junliang Zhang
September 2022, Molecules (Basel, Switzerland),
Deyun Qian, and Junliang Zhang
April 2011, The Journal of organic chemistry,
Copied contents to your clipboard!