A DFT study on gold-catalyzed domino cyclization for post-Ugi synthesis of spiroindolines: insights on the origin of remarkable diastereoselectivity

Abstract

We report a comprehensive DFT study on gold-catalyzed domino cyclization to spiroindolines. The diastereoselectivity was analyzed based on the established coordination spheres. These computational results not only explain the origin of diastereoselectivity of gold-catalyzed domino cyclization but also guide the development of more effective stereochemistry of transition metal complexes controlled by a counterion effect. Detailed analysis of the key intermediates and transition states showed that the preference of the domino cyclization could be attributed to both electronic and geometric factors.