A Counterion‐Directed Approach to the Diels–Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes | Zendy

Kiss Emily | Zendy; Campbell Craig D. | Zendy; Driver Russell W. | Zendy; Jolliffe John D. | Zendy; Lang Rosemary | Zendy; Sergeieva Tetiana | Zendy; Okovytyy Sergiy | Zendy; Paton Robert S. | Zendy; Smith Martin D. | Zendy

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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.

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