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.msm
gmail.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
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Abstract
An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-carbons 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
3,4-dihydro-2-pyridinones, lactams, organocatalysis, DPQ
ID: J54-Y2018
