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

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 C--C, C--H and C--X 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.