Metal-Free Regioselective Hydrophosphorodithioation of Spirovinylcyclopropyl Oxindoles: Rapid Access to Allyl Dialkylphosphorodithioates

Phosphorodithioates are important substructures due to their great use in bioactive compounds and functional materials. A metal-free 1,5-addition of spirovinylcyclopropyl oxindoles have been developed by choosing P4S10 and alcohol as nucleophiles through the regioselective ring-opening of spirovinyl...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-10, Vol.87 (19), p.12844-12853
Main Authors: Wang, Jiahua, Han, Fang, Hao, Siyuan, Tang, Yu-Jiang, Xiong, Cheng, Xiong, Lin, Li, Xiancheng, Lu, Jinrong, Zhou, Qingfa
Format: Article
Language:English
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Summary:Phosphorodithioates are important substructures due to their great use in bioactive compounds and functional materials. A metal-free 1,5-addition of spirovinylcyclopropyl oxindoles have been developed by choosing P4S10 and alcohol as nucleophiles through the regioselective ring-opening of spirovinylcyclopropyl oxindoles. This method provides access to allylic organothiophosphates with high efficiency, wide functional group tolerance, good chemo- and regioselectivity, and E-selectivity. 1,3-Addition products were also prepared in high yield. Furthermore, the resulting organothiophosphates could be readily transformed into other allylic derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01435