Phosphine-catalyzed [3+2] and [4+2] annulation reactions of ynones with barbiturate-derived alkenes

文献类型： 外文期刊

第一作者： Gao, Xing

作者： Gao, Xing;Li, Zhen;Yang, Wenjun;Liu, Yang;Chen, Wufeng;Zhang, Cheng;Guo, Hongchao;Zheng, Lufei;Guo, Hongchao

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期刊名称：ORGANIC & BIOMOLECULAR CHEMISTRY （ 影响因子：3.876； 五年影响因子：3.397 ）

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收录情况： SCI

摘要： The phosphine-catalyzed [3 + 2] annulation reaction of ynones and barbiturate-derived alkenes has been developed with the assistance of a weak acid, giving functionalized spirobarbiturate-cyclopentanones in moderate to excellent yields with excellent E/Z stereoselectivity. An unprecedented [4 + 2] annulation of ynones with barbiturate-derived alkenes was also achieved in the presence of a phosphine catalyst and an inorganic base, affording biologically interesting 1,5-dihydro-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione derivatives. An asymmetric variant of the [3 + 2] annulation reaction has been explored and a moderate enantioselectivity was obtained when a bifunctional chiral phosphine was used as a chiral catalyst. A plausible mechanism was proposed to illuminate two different reaction pathways.

分类号： O64

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