Enantioselectivity in Catalytic Asymmetric Fischer Indolizations Hinges on the Competition of π‑Stacking and CH/π Interactions

Abstract

Computational analyses of the first catalytic asymmetric Fischer indolization (<i>J. Am. Chem. Soc</i>. <b>2011</b>, <i>133</i>, 18534) reveal that enantioselectivity arises from differences in hydrogen bonding and CH/π interactions between the substrate and catalyst in the operative transition states. This selectivity occurs despite strong π-stacking interactions that reduce the enantioselectivity