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Huiqiang Wu,Xiangmin Wang,Yang Liu,Yu Zhao,Xinyue Wang,Woo-Kyoung Lee,심영기,Il Yoon,Xinming Xu,Jiazhu Li 대한화학회 2020 Bulletin of the Korean Chemical Society Vol.41 No.5
In this article, we report the stereoselective Horner?Wadsworth?Emmons reaction of reactive carbonyl-substituted chlorophyll a derivatives with diethyl cyanomethylphosphonate. We found that the formyl or keto group at the chlorin periphery can react stereoselectively with phosphonate carbanions to produce a series of cyanomethylene-substituted chlorins with predominantly E geometry. Considering that no consistent records are available in the literature on the results of the allomerization of methyl pyropheophorbide a, we propose a reliable process for the transformation of this chlorophyll derivative. Our methodology represents a simple and efficient way for the preparation of novel, differently functionalized long-wavelength absorbing chlorins, those can be applied for photodynamic therapy, solar cells, and other relevant purposes.