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

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

来源：Organic Letters, 2018, 20(1): 260-263.

DOI：10.1021/acs.orglett.7b03650

• N-HETEROCYCLIC CARBENE
• C-H BONDS
• BICYCLIC DELTA-LACTONES
• DIELS-ALDER REACTIONS
• BETA-FUNCTIONALIZATION
• ENANTIOSELECTIVE SYNTHESIS
• COOPERATIVE CATALYSIS
• C(SP(3))-H BONDS
• ALPHA,BETA-UNSATURATED ALDEHYDES
• SPIROOXINDOLE LACTONES

An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the beta-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert beta-sp(3) carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions.

• 出版日期2018-1-5
• 单位贵州大学