Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines

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 o...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-09, Vol.57 (7), p.8822-8825
Main Authors: Abazid, Ayham H, Nachtsheim, Boris J
Format: Article
Language:English
Subjects:
Chemical synthesis
Enantiomers
Naphthol
Substitutes
Triazoles
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Summary: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. A chiral iodane can oxidatively twist amide-substituted 2-naphthols into highly enantioenriched spirooxazolines.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc03246a