Generating Skeletal Diversity and Complexity from Boron-Substituted 1,3-Dienes and Enophiles

François, Benjamin; Eberlin, Ludovic; Berrée, Fabienne; Whiting, Andrew; Carboni, Bertrand

Abstract

Boron‐substituted 1,3‐dienes participate in ene reactions to afford new functionalized synthetic intermediates. After evaluating several enophiles as partners, the resulting products have been engaged in multistep sequences involving first a Diels Alder/allyboration process. A variety of skeletally diverse and complex polycyclic heterocycles were thus synthesized, such as tetrahydro‐ 1H ‐isoindole‐1,3( 2H )‐diones, eight‐membered lactones or tricyclic spiro compounds.

Citation

François, B., Eberlin, L., Berrée, F., Whiting, A., & Carboni, B. (2020). Generating Skeletal Diversity and Complexity from Boron-Substituted 1,3-Dienes and Enophiles. European Journal of Organic Chemistry, 2020(22), 3282-3293. https://doi.org/10.1002/ejoc.202000330

• Journal Article Type: Article
• Acceptance Date: Apr 24, 2020
• Online Publication Date: May 27, 2020
• Publication Date: Jun 1, 2020
• Deposit Date: Apr 30, 2020
• Publicly Available Date: May 27, 2021
• Journal: European Journal of Organic Chemistry
• Print ISSN: 1434-193X
• Electronic ISSN: 1099-0690
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 2020
• Issue: 22
• Pages: 3282-3293
• DOI: https://doi.org/10.1002/ejoc.202000330
• Public URL: https://durham-repository.worktribe.com/output/1271575