"The Diels-Alder reaction is a powerful tool in organic synthesis that may be used to create a variety of diverse products varying in complexity and the option of generating up to four new chiral centers. Intramolecular Diels-Alder reactions of dienynes have been widely explored with the exception of substrates containing an electron-withdrawing group on the diene portion of the molecule, due to the known poor reactivity of these particular electron-deficient dienynes. In our efforts, we have recently discovered optimal conditions for an efficient formal intramolecular Diels-Alder (FIMDA) cyclization and oxidation of electron-deficient dienynes to their corresponding indane-ester products. By employing a rhodium catalyst and silver additive in this [4 + 2] process, we have developed a robust and concise method for achieving complex 5,6-bicyclic structures via electron poor dienynes. Notably, this reaction may serve as an efficient method for the synthesis of a variety of biologically intriguing sesquiterpene scaffolds."

Efficient Formal Intramolecular Diels-Alder (FIMDA) cyclization of electron-deficient dienynes

253rd National Meeting (2017)

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