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Benzyne-Promoted Curtius-Type Rearrangement of Acyl Hydrazides in the Presence of Nucleophiles
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2017-11-16 09:21:02 , DOI: 10.1002/ajoc.201700598
Jing-Yu Guo 1 , Chen-Hao Zhong 1 , Zeng-Yang He 1 , Shi-Kai Tian 1
Affiliation  

Curtius-type rearrangement: A wide variety of N′-methyl-N′-phenyl acyl hydrazides were treated with oxygen, nitrogen, or sulfur nucleophiles in the presence of 2-(trimethylsilyl)phenyl triflate and CsF under mild conditions to afford structurally diverse carbamates or analogues. Importantly, complete retention of configuration was observed in the reaction of enantioenriched α-chiral alkanoyl hydrazides.

中文翻译:

在亲核试剂存在下,苯并炔促进的乙酰肼的库蒂斯型重排

Curtius型重排:在2-(三甲基甲硅烷基)苯基三氟甲磺酸酯和CsF存在下,在温和条件下,用氧,氮或硫亲核试剂处理多种N'-甲基-N'-苯基酰基酰肼,以提供结构多样的氨基甲酸酯或类似物。重要的是,在对映体富集的α-手性链烷酰基酰肼的反应中观察到构型的完全保留。
更新日期:2017-11-16
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