Efficient Synthesis of Long-wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner-Wadsworth-Emmons Reaction
Efficient Synthesis of Long-wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner-Wadsworth-Emmons Reaction
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通过立体选择性 Horner-Wadsworth-Emmons 反应高效合成长波长吸收氰基叶绿素 a 衍生物
DOI：
10.1002/bkcs.11998
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发表时间：
2020
影响因子：
1.7
通讯作者：
Li Jiazhu
中科院分区：
文献类型：
--
作者：
Wu Huiqiang;Wang Xiangmin;Liu Yang;Zhao Yu;Wang Xinyue;Lee Woo Kyoung;Shim Young Key;Yoon Il;Xu Xinming;Li Jiazhu
在这篇文章中，我们报道了反应性羰基取代的叶绿素衍生物与氰基甲基膦酸二乙酯的立体选择性Horner-Wadsworth-Emmons反应。我们发现，二氢卟酚外围的甲酰基或酮基可以立体选择性地与膦酸酯碳负离子反应，生成一系列以E几何构型为主的氰基亚甲基取代的二氢卟酚。考虑到没有一致的记录是在文献中的甲基pyropheophorbidea的异构化的结果，我们提出了一个可靠的方法，这种叶绿素衍生物的转化。我们的方法代表了一种简单有效的方法来制备新型、不同功能化的长波长吸收二氢黄酮，这些二氢黄酮可应用于光动力治疗、太阳能电池和其他相关用途。
In this article, we report the stereoselective Horner–Wadsworth–Emmons reaction of reactive carbonyl‐substituted chlorophylladerivatives 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 predominantlyEgeometry. Considering that no consistent records are available in the literature on the results of the allomerization of methyl pyropheophorbidea, 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.