Enantioselectivity in Catalytic Asymmetric Fischer Indolizations Hinges on the Competition of π-Stacking and CH/π Interactions
2015
Seguin, Trevor J. | Lu, Tongxiang | Wheeler, Steven E.
Computational analyses of the first catalytic asymmetric Fischer indolization (J. Am. Chem. Soc. 2011, 133, 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.
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