Strategy for Stereoselective Metal-free -Functionalization of 2-Azaaryl Acetates with N-Boc Imines
Strategy for Stereoselective Metal-free -Functionalization of 2-Azaaryl Acetates with N-Boc Imines
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DOI：
10.1002/chem.201703748
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发表时间：
2017-09-27
影响因子：
4.3
通讯作者：
Palomo, Claudio
中科院分区：
文献类型：
--
作者：
Bastida, Inaki;San Segundo, Marcos;Palomo, Claudio
我们报道了第一个非映对和对映选择性的2-吡啶乙酸酯的形式曼尼希反应，它产生了-和-功能化的2-取代吡啶。成功的关键是先前的氮杂芳烃n -氧化物的形成，使-碳在温和的双功能BrOnsted碱中去质子化，随后与N-Boc亚胺在几乎完美的立体控制下反应。
We report the first diastereo- and enantioselective formal Mannich reaction of 2-pyridyl acetates which gives rise to - and -functionalized 2-substituted pyridines. Key for success is the previous azaarene N-oxide formation enabling -carbon deprotonation by a mild bifunctional BrOnsted base and subsequent reaction with N-Boc imines under almost perfect stereocontrol.