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Ommidala Pattawong, Thomas J. L. Mustard, Ryne C. Johnston and Prof. Paul Ha-Yeon Cheong Mechanism and Stereocontrol: Enantioselective Addition of Pyrrole to Ketenes Using Planar-Chiral Organocatalysts Angewandte Chemie International Edition 52

Version of Record online: 13 DEC 2012 | DOI: 10.1002/anie.201208417

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In control: The computational study of the title reaction catalyzed by the planar-chiral 4-(pyrrolidino)pyridine is reported (see scheme). The resting state is a chiral Brønsted acid complex and the rate-determining step involves a chiral base. The catalyst controls the enantioselectivity through a combination of stereoelectronic effects and CH⋅⋅⋅O interactions.

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