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Palladium‐Catalyzed Enantioselective Reductive Heck Reactions: Convenient Access to 3,3‐Disubstituted 2,3‐Dihydrobenzofuran
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-07-15 , DOI: 10.1002/anie.201806372
Zhan-Ming Zhang 1 , Bing Xu 1 , Yanyan Qian 2 , Lizuo Wu 2 , Yuanqi Wu 2 , Lujia Zhou 1 , Yu Liu 2 , Junliang Zhang 1, 3
Affiliation  

The first example of highly enantioselective intramolecular hydroarylation of allyl aryl ethers was realized by palladium‐catalyzed reductive heck reactions utilizing a new chiral sulfinamide phosphine ligand (N‐Me‐XuPhos). N‐Me‐XuPhos can be easily prepared on gram scale from readily available starting materials in a one‐pot synthesis approach. A series of optically active 2,3‐dihydrobenzofurans bearing a quaternary stereocenter were obtained in good yields and with excellent enantioselectivities. The practicality of this reaction was validated in the straightforward synthesis of CB2 receptor agonists. Moreover, deuterium was efficiently incorporated into the products.

中文翻译:

钯催化的对映选择性还原Heck反应:方便地获得3,3-二取代的2,3-二氢苯并呋喃

烯丙基芳基醚的高对映选择性分子内氢芳基化反应的第一个例子是通过使用新的手性亚磺酰胺膦配体(N- Me - XuPhos)进行钯催化的还原性heck反应而实现的。N- Me - XuPhos可以通过一锅合成方法轻松地从容易获得的起始原料中以克为单位制备。以良好的收率和优异的对映选择性获得了一系列带有季立体中心的旋光2,3-二氢苯并呋喃。该反应的实用性已在CB2受体激动剂的直接合成中得到验证。此外,将氘有效地掺入了产品中。
更新日期:2018-07-15
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