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Direct Activation of β-sp3-Carbons of Saturated Carboxylic Esters as Electrophilic Carbons via Oxidative Carbene Catalysis

Bin Liu, Weihong Wang, Ruoyan Huang, Jiekuan Yan, Jichang Wu, Wei Xue, Song Yang*, Zhichao Jin and Yonggui Robin Chi*

*Guizhou University, Huaxi District, Guiyang 550025, China; Nanyang Technological University, Singapore 637371, Singapore, Email: jhzx.msmgmail.com, robinchintu.edu.sg

B. Liu, W. Wang, R. Huang, J. Yan, J. Wu, W. Xue, S. Yang, Z. Jin, Y. R. Chi, Org. Lett., 2018, 20, 260-263.

DOI: 10.1021/acs.orglett.7b03650 (free Supporting Information)


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Abstract

An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters enables an efficient asymmetric access to lactams and lactones. The method introduces functional groups at the typically inert β-sp3 carbons of saturated esters. The use of HOBt as an additive improves both yields and enantioselectivities of the reactions.

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proposed mechanism



Key Words

N-heterocycles, lactams, organocatalysis, DPQ


ID: J54-Y2018