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Mechanism and Stereocontrol: Enantioselective Addition of Pyrrole to Ketenes Using Planar‐Chiral Organocatalysts
Author(s) -
Pattawong Ommidala,
Mustard Thomas J. L.,
Johnston Ryne C.,
Cheong Paul HaYeon
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201208417
Subject(s) - enantioselective synthesis , pyridine , catalysis , chemistry , pyrrole , brønsted–lowry acid–base theory , combinatorial chemistry , stereochemistry , planar chirality , organic chemistry
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.