Mechanism and Stereocontrol: Enantioselective Addition of Pyrrole to Ketenes Using Planar‐Chiral Organocatalysts | Zendy

Pattawong Ommidala | Zendy; Mustard Thomas J. L. | Zendy; Johnston Ryne C. | Zendy; Cheong Paul HaYeon | Zendy

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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.

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