Ring strain strategy for the control of regioselectivity. Gold-catalyzed anti-Markovnikov cycloisomerization initiated tandem reactions of alkynes

Chao Shu; Long Li; Tong-De Tan; Ding-Qiang Yuan; Long-Wu Ye

doi:10.1016/j.scib.2017.01.016

Ring strain strategy for the control of regioselectivity. Gold-catalyzed anti-Markovnikov cycloisomerization initiated tandem reactions of alkynes

Sci Bull (Beijing). 2017 Mar 1;62(5):352-357. doi: 10.1016/j.scib.2017.01.016. Epub 2017 Jan 18.

Authors

Chao Shu¹, Long Li¹, Tong-De Tan¹, Ding-Qiang Yuan¹, Long-Wu Ye²

Affiliations

¹ State Key Laboratory of Physical Chemistry of Solid Surfaces and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
² State Key Laboratory of Physical Chemistry of Solid Surfaces and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address: longwuye@xmu.edu.cn.

PMID: 36659420
DOI: 10.1016/j.scib.2017.01.016

Abstract

Gold-catalyzed nucleophilic addition to terminal alkynes has received considerable interest in the past decade, as this chemistry offers a highly efficient and regioselective way for CC, CH and CX bond formation. However, such a nucleophilic addition mainly involves a Markovnikov addition. In this short review, the recent progress of the gold-catalyzed 5-endo-dig cycloisomerization-initiated tandem reactions by utilizing the steric strain in ring formation to achieve an anti-Markovnikov regioselectivity was reviewed, including the scope of reactions, mechanism and synthetic applications.

Keywords: Cyclization; Gold; Heterocycles; Ring strain; Tandem reaction.

Publication types

Review