Cycloaddition and Pericyclic Reactions

Cycloaddition reactions build ring-containing molecules by simultaneously creating two bonds between reacting molecules.  Usually, two molecules with π-bonding combine to form a new cyclic molecule with reduced π-bonding.  The most common cycloaddition reaction is the Diels-Alder reaction where a conjugated diene (2 π-bonds) reacts with an alkene (1 π-bond) to form a cyclohexene derivative (1 π-bond). Used appropriately, they provide a rapid means of generating molecular complexity in a controlled and predictable manner.  For this reason, they are widely used in industry for the synthesis of medicines and agrochemicals.

Key Abstracts

Total Synthesis of (-)-Colombiasin A and (-)-Elisapterosin B

D.C. Harrowven, D.D. Pascoe, D. Demurtas, H.O. Bourne, Angew. Chem,  2005, 117, 1247-1248

A Thermally Induced Hydride Transfer from an Amine to an Allene Triggers an Annulation Reaction, Giving Dihydrofuropyridinones

Wei SunDharyl C. WilsonMark E. Light, and David C. Harrowven, Organic Letters 2018, 20, (14) 4346-4349

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