Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Angewandte Chemie (International ed.), 2016-10, Vol.55 (44), p.13813-13817

Auflage

International ed. in English

Ort / Verlag

Germany: Blackwell Publishing Ltd

Erscheinungsjahr

2016

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Role play: 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/epimerization/cyclopropanation cascade in which size and coordination of the achiral counterion plays a key role in the stereochemical outcome of the reaction.