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

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posted on 18.12.2015, 00:00 by Yi-Fei Liu, Zhen Wang, Jin-Wei Shi, Bai-Ling Chen, Zhi-Gang Zhao, Zili Chen
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.