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Efficient Synthesis of Long‐wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner–Wadsworth–Emmons Reaction
Author(s) -
Wu Huiqiang,
Wang Xiangmin,
Liu Yang,
Zhao Yu,
Wang Xinyue,
Lee Woo Kyoung,
Shim Young Key,
Yoon Il,
Xu Xinming,
Li Jiazhu
Publication year - 2020
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11998
Subject(s) - stereoselectivity , phosphonate , chemistry , carbanion , derivative (finance) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics
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.