NHC-Ag(I)-Catalyzed Three-Component 1,3-Dipolar Cycloaddition To Provide Polysubstituted Dihydro-/Tetrahydrofurans

A new method was developed to synthesize polyfunctionalized dihydrofuran and tetrahydrofuran derivatives from the three-component [2 + 2 + 1] cycloaddition of the diazoesters with aryl/alkenyl aldehydes and alkyne/olefin dipolarophiles by using a Ag­(I) N-heterocyclic carbene complex as the catalyst...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-12, Vol.80 (24), p.12733-12739
Main Authors: Liu, Yi-Fei, Wang, Zhen, Shi, Jin-Wei, Chen, Bai-Ling, Zhao, Zhi-Gang, Chen, Zili
Format: Article
Language:English
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Summary:A new method was developed to synthesize polyfunctionalized dihydrofuran and tetrahydrofuran derivatives from the three-component [2 + 2 + 1] cycloaddition of the diazoesters with aryl/alkenyl aldehydes and alkyne/olefin dipolarophiles by using a Ag­(I) N-heterocyclic carbene complex as the catalyst. A carbonyl ylide intermediate was generated, which undertook an endo-type 1,3-dipolar cycloaddition to provide the desired dihydro-/tetrahydrofurans in high regio- and diastereoselectivities by using α-aryl or α-alkenyl diazoesters.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02422