Highly Regio- and Enantioselective Nitroso Diels−Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral N,N′-Dioxide/Copper(II) Complex,Advanced Synthesis & Catalysis

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Highly Regio- and Enantioselective Nitroso Diels−Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral N,N′-Dioxide/Copper(II) Complex
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-11-13 10:52:38 , DOI: 10.1002/adsc.201701155
Yan Lu ₁ , Yuhang Zhou ₁ , Jingchuan Zhang ₁ , Lili Lin ₁ , Xiaohua Liu ₁ , Xiaoming Feng _{1,

2}

Affiliation

A chiral N,N′-dioxide/Copper(II) complex-catalyzed highly regio- and enantioselective nitroso Diels−Alder (NDA) reaction of 2-nitrosopyridines with 1,3-diene-1-carbamates was described. A series of 3,6-dihydro-1,2-oxazines were obtained in good to excellent yields and ee values. On the basis of the control experiments, ESI-MS analysis and the absolute configuration of the product, a possible transition state model was proposed to explain the stereocontrol.

中文翻译：

手性N，N'-二氧化物/铜（II）配合物催化1,3-二烯-1-氨基甲酸酯的高区域和对映选择性亚硝基Diels-Alder反应

描述了手性N，N'-二氧化物/铜（II）络合物催化的2-亚硝基吡啶与1,3-二烯-1-氨基甲酸酯的高度区域和对映选择性亚硝基Diels-Alder（NDA）反应。获得了一系列3,6-二氢-1,2-恶嗪，收率和ee值都非常好。在控制实验，ESI-MS分析和产品的绝对配置的基础上，提出了可能的过渡态模型来解释立体控制。

更新日期：2017-11-13

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