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Chiral Ferrocenyl P,N-Ligands for Palladium-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Propargylic Esters with β-Ketoesters: Access to Functionalized Chiral 2,3-Dihydrofurans

Yong Zhou, Fu-Lin Zhu, Zhen-Ting Liu, Xiao-Mao Zhou* and Xiang-Ping Hu*

*Hunan Academy of Agricultural Sciences, Changsha 410125; Chinese Academy of Sciences, Dalian 116023, China, Email: zhouxm1972126.com, xiangpingdicp.ac.cn

Y. Zhou, F.-L. Zhu, Z.-T. Liu, X.-M. Zhou, X.-P. Hu, Org. Lett., 2016, 18, 2734-2737.

DOI: 10.1021/acs.orglett.6b01192 (free Supporting Information)


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Abstract

A chiral ferrocene/benzimidazole-based P,N-ligand enables a highly enantioselective palladium-catalyzed [3 + 2] cycloaddition of propargylic esters with β-ketoesters providing 2,3-dihydrofurans bearing an exocyclic double bond at the 3-position in good yields and with high enantioselectivities. This protocol tolerates a broad range of functional groups in both propargylic esters and β-ketoesters.


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Key Words

2,3-dihydrofurans


ID: J54-Y2016