Palladium‐Catalyzed Intramolecular Trost–Oppolzer‐Type Alder–Ene Reaction of Dienyl Acetates to Cyclopentadienes. (4th January 2018)

• Record Type: Journal Article
• Authors: Bankar, Siddheshwar K.; Singh, Bara; Tung, Pinku; Ramasastry, S. S. V.
• Is Part Of: Angewandte Chemie. Volume 130:Number 6(2018)
• Page Start: 1694
• Page End: 1698
• Publication Date: 2018-01-04
• Subjects: Cyclopentadiene -- Heterocyclen -- Indane -- Palladium -- Tsuji-Trost-Reaktion; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201711797
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A new approach to the synthesis of highly substituted cyclopentadienes, indenes, and cyclopentene‐fused heteroarenes by means of the Pd‐catalyzed Trost–Oppolzer‐type intramolecular Alder–ene reaction of 2, 4‐pentadienyl acetates is described. This unprecedented transformation combines the electrophilic features of the Tsuji–Trost reaction with the nucleophilic features of the Alder–ene reaction. The overall outcome can be perceived as a hitherto unknown "acid‐free" iso‐Nazarov‐type cyclization. The versatility of this strategy was further demonstrated by the formal synthesis of paucifloral F, a resveratrol‐based natural product.