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Utilization of fluoroform for difluoromethylation in continuous flow: a concise synthesis of α-difluoromethyl-amino acids
Green Chemistry ( IF 9.8 ) Pub Date : 2017-10-30 00:00:00 , DOI: 10.1039/c7gc02913f
Manuel Köckinger 1, 2, 3, 4, 5 , Tanja Ciaglia 1, 2, 3, 4, 5 , Michael Bersier 6, 7, 8, 9 , Paul Hanselmann 6, 7, 8, 9 , Bernhard Gutmann 1, 2, 3, 4, 5 , C. Oliver Kappe 1, 2, 3, 4, 5
Affiliation  

Fluoroform (CHF3) can be considered as an ideal reagent for difluoromethylation reactions. However, due to the low reactivity of fluoroform, only very few applications have been reported so far. Herein we report a continuous flow difluoromethylation protocol on sp3 carbons employing fluoroform as a reagent. The protocol is applicable for the direct Cα-difluoromethylation of protected α-amino acids, and enables a highly atom efficient synthesis of the active pharmaceutical ingredient eflornithine.

中文翻译:

氟仿连续流动中二氟甲基化的应用:α-二氟甲基氨基酸的简明合成

氟仿(CHF 3)被认为是二氟甲基化反应的理想试剂。然而,由于氟仿的低反应性,迄今为止仅报道了很少的应用。在本文中,我们报告了使用氟仿作为试剂在sp 3碳上连续流动的二氟甲基化方案。该协议是适用于直接Ç α保护的α氨基酸的-difluoromethylation,并且使活性药物成分依氟鸟氨酸的高度原子有效合成。
更新日期:2018-01-02
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