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A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes.

ABSTRACT: 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.

SUBMITTER: Kiss E

PROVIDER: S-EPMC5113799 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes.

Kiss Emily E Campbell Craig D CD Driver Russell W RW Jolliffe John D JD Lang Rosemary R Sergeieva Tetiana T Okovytyy Sergiy S Paton Robert S RS Smith Martin D MD

Angewandte Chemie (International ed. in English) 20161007 44

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. ...[more]

PMID: 27714921

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