首页|Catalytic Asymmetric Synthesis of Inherently Chiral Saddle-Shaped Dibenzo[b,f][1,5]diazocines

Catalytic Asymmetric Synthesis of Inherently Chiral Saddle-Shaped Dibenzo[b,f][1,5]diazocines

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Dibenzo[b,f][1,5]diazocines are a class of eight-membered heterocycles,which exhibit unique rigid saddle-shaped structure and pos-sess inherent chirality.In this study,we report a convenient and straightforward method for the catalytic enantioselective synthesis of these unique chiral molecules through chiral phosphoric acid-catalyzed dimerization of 2-acylbenzoisocyanates.Notably,the addition of corresponding 2-acylaniline as the co-catalyst significantly improved the efficiency of these reactions,and a simple phase separa-tion operation resulted in products with excellent enantiopurity.Experimental studies were performed to elucidate the mechanism behind these reactions,leading to the proposal of a plausible reaction mechanism based on the study findings.

Dibenzo[b,f][1,5]diazocinesSaddle-shaped inherent chiralityOrganocatalysisAsymmetric catalysisMedium-ring compoundsCooperative catalysisChiral phosphoric acids

Jinmiao Zhou、Mengyao Tang、Xiaoyu Yang

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School of Physical Science and Technology,ShanghaiTech University,Shanghai 201210,China

2024

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子:0.848
ISSN:1001-604X
年,卷(期):2024.42(17)