期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 9, 页码 2469-2472出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611816
关键词
azomethine ylides; cycloaddition; gold; heterocycles; synthetic methods
资金
- Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT)
- MEXT-supported Program for the Strategic Research Foundation at Private Universities
- Uehara Memorial Foundation
- Grants-in-Aid for Scientific Research [15K07877] Funding Source: KAKEN
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.
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