Synthesis of 2,5-Dihydrofurans via a Gold(I)-Catalyzed Formal [4 + 1] Cycloaddition of α-Diazoesters and Propargyl Alcohols
Jing Wang, Xinbo Yao, Tao Wang*, Jie Han, Jin Zhang, Xi Zhang, Ping Wang and Zunting Zhang*
*School of Chemistry and Chemical Engineering, Shaanxi Normal University, No.620 West Chang’an Avenue, Xi’an 710119, China, Email: chemtaosnnu.edu.cn, zhangzuntingsina.com
J. Wang, X. Yao, T. Wang, J. Han, J. Han, J. Zhang, X. Zhang, P. Wang, Z. Zhang, Org. Lett., 2015, 17, 5124-5127.
DOI: 10.1021/acs.orglett.5b02663 (free Supporting Information)
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A gold(I)-catalyzed formal [4 + 1] cycloaddition of α-diazoesters and propargyl alcohols provides various 2,5-dihydrofurans with a broad substrate scope and functional group tolerance. Preliminary mechanistic investigation indicates that this reaction most likely occurs through a 5-endo-dig cyclization of an α-hydroxy allene intermediate.
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