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Bifunctional catalysis in the stereocontrolled synthesis of tetrahydro-1,2-oxazines†
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-12-08 00:00:00 , DOI: 10.1039/c7ob02894f
Marek Moczulski 1, 2, 3, 4, 5 , Piotr Drelich 1, 2, 3, 4, 5 , Łukasz Albrecht 1, 2, 3, 4, 5
Affiliation  

This study demonstrates that the annulation of a tetrahydro-1,2-oxazine ring can be realized via bifunctional catalysis, employing nitroolefins and a recently introduced group of aminooxylating reagents as starting materials. The developed cascade reactivity proceeds in a sequence aza-Michael–Michael reaction. The target products, bearing three contiguous stereocenters, have been obtained with high yields (up to 97%) and excellent stereocontrol (>20 : 1 dr, up to 99.5 : 0.5 er).

中文翻译:

四氢1,2-恶嗪的立体控制合成中的双功能催化

这项研究表明,使用硝基烯烃和最近引入的一组氨基氧化试剂作为起始原料,可以通过双功能催化实现四氢1,2-恶嗪环的环化。所发展的级联反应性按序列aza-Michael-Michael反应进行。获得了具有三个连续立体中心的目标产品,具有高产率(高达97%)和出色的立体控制(> 20:1 dr,高达99.5:0.5 er)。
更新日期:2017-12-08
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