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A Counterion‐Directed Approach to the Diels–Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes
Author(s) -
Kiss Emily,
Campbell Craig D.,
Driver Russell W.,
Jolliffe John D.,
Lang Rosemary,
Sergeieva Tetiana,
Okovytyy Sergiy,
Paton Robert S.,
Smith Martin D.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608534
Subject(s) - stereocenter , cyclopropanation , intramolecular force , cascade , counterion , chemistry , diels–alder reaction , michael reaction , epimer , stereochemistry , cascade reaction , computational chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , ion , chromatography
An approach to the intramolecular Diels–Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds by a Michael/Michael/cyclopropanation/epimerization cascade in which size and coordination of the counterion is key.