Diastereoselective, Lewis acid-mediated Diels-Alder reactions of allenoic acid derivatives and 1,3-cyclopentadienes

Freya M. Harvey, Alexandra H. Heidecker, Christian Merten, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

Abstract

Allenes with different substituents at their terminal carbon atom display axial chirality and can be obtained in enantiopure form by a photochemical deracemization protocol. It has now been studied under which conditions allenoic acid derivatives undergo a Diels-Alder reaction with 1,3-cyclopentadienes and which products result. Cyclic derivatives (lactams, lactones) underwent an exo-selective reaction catalyzed by the Lewis acid Eu(fod)3, while acyclic derivatives yielded with high preference the endo-products (EtAlCl2 as the preferred Lewis acid). The exocyclic double bond forms with exquisite diastereoselectivity and the chirality transfer is close to perfect. The method was applied to the synthesis of the sesquiterpenes β-santalol (1) and 10(E)-β-santalic acid (13).

Original languageEnglish
Pages (from-to)4422-4428
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume21
Issue number21
DOIs
StatePublished - 8 May 2023

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