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

Author:
Liu, Yi-Fei, Wang, Zhen, Shi, Jin-Wei, Chen, Bai-Ling, Zhao, Zhi-Gang, Chen, Zili
Source:
Journal of organic chemistry 2015 v.80 no.24 pp. 12733-12739
ISSN:
1520-6904
Subject:
aldehydes, alkynes, carbenes, catalysts, chemical reactions, chemical structure, heterocyclic nitrogen compounds, methodology, olefin, organic chemistry, silver, tetrahydrofuran
Abstract:
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.
Agid:
5505016