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Carbene-Catalyzed Enantioselective Synthesis of γ-Keto-β-silyl Esters and Amides

Yuxia Zhang, Xuan Huang, Jingcheng Guo, Chenlong Wei, Minghua Gong and Zhenqian Fu*

*Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, China, Email: iamzqfunjtech.edu.cn

Y. Zhang, X. Huang, J. Guo, C. Wei, M. Gong, Z. Fu, Org. Lett., 2020, 22, 9545-9550.

DOI: 10.1021/acs.orglett.0c03589


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Abstract

An efficient carbene-catalyzed formal [4 + 2] annulation of β-silyl enones with a HOBT ester followed by ring opening with nucleophiles provides γ-keto-β-silyl esters and amides, most with extremely high enantioselectivities. γ-Keto-β-silyl esters can be easily converted into enantioenriched β,σ-dihydroxyl esters.


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proposed mechanism



Key Words

β-hydroxy esters, 1,5-keto esters, organocatalysis


ID: J54-Y2020