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Gold‐Catalyzed [3+2]/Retro‐[3+2]/[3+2] Cycloaddition Cascade Reaction of N ‐Alkoxyazomethine Ylides
Author(s) -
Sugita Shoichi,
Takeda Norihiko,
Tohnai Norimitsu,
Miyata Mikiji,
Miyata Okiko,
Ueda Masafumi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611816
Subject(s) - cycloaddition , chemistry , ylide , bond cleavage , catalysis , cascade , intermolecular force , triple bond , combinatorial chemistry , stereochemistry , double bond , molecule , organic chemistry , chromatography
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.