Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes

Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes
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钯催化 1,3-二烯的不对称氨基羟基化

DOI:
10.1002/anie.201712350
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发表时间:
2018
期刊:
Angewandte Chemie International Edition
影响因子:
--
通讯作者:
Gong Liu-Zhu
Gong Liu-Zhu
中科院分区:
其他
文献类型:
--
作者:
Shen Hong-Cheng;Wu Yu-Feng;Zhang Ying;Fan Lian-Feng;Han Zhi-Yong;Gong Liu-Zhu

文献摘要

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用手性吡啶双(恶唑啉)配体催化1,3-二烯与N-对甲苯磺基-2-氨基苯酚的不对称氨羟化反应。这种高区域选择性的反应提供了直接和高效的手性3,4-二氢-2H-1,4-苯并恶嗪的合成途径,产率高,对映体选择性高(高达96:4E.R.)。该反应使用了易得的N-对甲苯磺基-2-氨基苯酚作为唯一的氨基羟化试剂,并补充了已知的不对称氨羟化方法。
A PdII‐catalyzed asymmetric aminohydroxylation of 1,3‐dienes with N‐tosyl‐2‐aminophenols was developed by making use of a chiral pyridinebis(oxazoline) ligand. The highly regioselective reaction provides direct and efficient access to chiral 3,4‐dihydro‐2H‐1,4‐benzoxazines in high yield and enantioselectivity (up to 96:4 e.r.). The reaction employs readily available N‐tosyl‐2‐aminophenols as a unique aminohydroxylation reagent and is complementary to known asymmetric aminohydroxylation methods.