期刊
ORGANIC CHEMISTRY FRONTIERS
卷 9, 期 15, 页码 3990-3997出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00775d
关键词
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资金
- National Natural Science Foundation of China [22193011, 21971120, 21933008]
- National Science & Technology Fundamental Resource Investigation Program of China [2018FY201200]
- Haihe Laboratory of Sustainable Chemical Transformations
A practical and efficient method for the asymmetric difluorocarbonylation reaction of non-active imines with difluoroenoxysilane has been reported, yielding products with high efficiency and enantioselectivity. The method can also be applied to other compounds and the synthetic utility of the products has been demonstrated through diverse transformations.
Difluorinated carbonyl has been identified as the basic skeleton of multitudinous biologically active molecules. However, development of strategies for asymmetrically introducing such an important moiety remains a formidable challenge. Herein, we reported a practical and efficient asymmetric difluorocarbonylation reaction of non-active imines with difluoroenoxysilane. In the presence of Bi(OAc)(3)/chiral phosphoric acid (2 mol%), excellent efficiency (up to 99%) and high enantioselectivity (up to 99 : 1 e.r.) were obtained. The reaction could be scaled up, and the synthetic utility of the desired chiral difluorocarbonylation product was proved by diverse transformations. In addition, the catalytic strategy can also be well applied to other imines, oxocarbenium ions and monofluorinated enol silyl ether. A possible mechanism is proposed to illustrate the reaction process and density functional theory calculation is conducted to interpret the enantioselectivity.
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