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Iodine as Polarity-Reversal Catalyst: Synthesis of a Fused Heterocycle with Contiguous Stereocenters
Organic Letters ( IF 4.9 ) Pub Date : 2024-12-20 , DOI: 10.1021/acs.orglett.4c03936 Li-Sheng Wang, Yu-Man Song, You Zhou, Yong-Xing Tang, Chun-Yan Wu, Zhi-Cheng Yu, Hui Zhou, Kai-Lu Zheng, An-Xin Wu
Organic Letters ( IF 4.9 ) Pub Date : 2024-12-20 , DOI: 10.1021/acs.orglett.4c03936 Li-Sheng Wang, Yu-Man Song, You Zhou, Yong-Xing Tang, Chun-Yan Wu, Zhi-Cheng Yu, Hui Zhou, Kai-Lu Zheng, An-Xin Wu
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We report an unconventional I2-catalyzed cascade reaction for the synthesis of angular triquinane derivatives with a fused heterocycle skeleton, leveraging enaminones and anilines as simple acyclic precursors. The key to success lies in I2 functioning as a polar-reversal catalyst, which alters the reactivity at the α-position of the enaminone and facilitates the first hexa-functionalization of an enaminone along with the formation of highly congested continuous stereocenters.
更新日期：2024-12-20
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