Chinese Journal of Organic Chemistry >
N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones
Received date: 2021-05-01
Revised date: 2021-07-05
Online published: 2021-07-26
Supported by
National Natural Science Foundation of China(21602105)
Asymmetric synthesis of chiral organosilanes with a potential application was realized by N-heterocyclic carbene- catalyzed [4+2] annulation of acetates and β-silyl enones. This strategy exhibits easy to obtain raw materials, mild reaction conditions, good substrate tolerance, simple operation and so on. Notably, excellent yield and enantioselectivity were also observed with expanding the reaction scale by 10 times. The target product showed excellent results in hydrogenation reduction. Moreover, the hypolipidemic drug ezetimibe was obtained through the synthetic transformation of the resulting products.
Yuxia Zhang , Jingcheng Guo , Jie Huang , Zhenqian Fu . N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4467 -4475 . DOI: 10.6023/cjoc202105002
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