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- Title
Gold-Catalyzed [3+2]/Retro-[3+2]/[3+2] Cycloaddition Cascade Reaction of N-Alkoxyazomethine Ylides.
- Authors
Sugita, Shoichi; Takeda, Norihiko; Tohnai, Norimitsu; Miyata, Mikiji; Miyata, Okiko; Ueda, Masafumi
- Abstract
A novel cascade reaction has been developed for the synthesis of 2,6-methanopyrrolo[1,2-b]isoxazoles based on the gold-catalyzed generation of an N-allyloxyazomethine ylide. This reaction involves sequential [3+2]/retro-[3+2]/[3+2] cycloaddition reactions, thus providing facile access to fused and bridged heterocycles which would be otherwise difficult to prepare using existing synthetic methods. Notably, this reaction allows the efficient construction of three C−C bonds, one C−O bond, one C−N bond and one C−H bond, as well as the cleavage of one C−C bond, one C−O bond and one C−H bond in a single operation. The intermolecular cycloaddition of an N-allyloxyazomethine ylide and the subsequent application of the product to the synthesis of tropenol is also described.
- Subjects
GOLD catalysts; RING formation (Chemistry); YLIDES; HETEROCYCLIC compounds; CHEMICAL synthesis
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 9, p2469
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201611816