Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines. Issue 70 (12th August 2021)

• Record Type: Journal Article
• Authors: Abazid, Ayham H.; Nachtsheim, Boris J.
• Is Part Of: Chemical communications. Volume 57:Issue 70(2021)
• Page Start: 8822
• Page End: 8825
• Publication Date: 2021-08-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc03246a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A chiral iodane can oxidatively twist amide-substituted 2-naphthols into highly enantioenriched spirooxazolines. Abstract : A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can be isolated through an enantioselective oxidative dearomatization in up to 92% yield and 97% ee. The further synthetic utility of the optically enriched spirooxazolines was examined providing a corresponding 2-naphthalenole and an oxepin.