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Pd‐Catalyzed Enantioselective [6+4] Cycloaddition of Vinyl Oxetanes with Azadienes to Access Ten‐Membered Heterocycles
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-01-15 , DOI: 10.1002/anie.201711648
Ya-Nong Wang 1 , Li-Cheng Yang 1 , Zi-Qiang Rong 1 , Tang-Lin Liu 1 , Ruoyang Liu 1 , Yu Zhao 1
Affiliation  

We report herein the first enantioselective cycloaddition of vinyl oxetanes, the reaction of which with azadienes provided unprecedented access to ten‐membered heterocycles through a [6+4] cycloaddition. By using a commercially available chiral Pd‐SIPHOX catalyst, a wide range of benzofuran‐ as well as indole‐fused heterocycles could be accessed in excellent yield and enantioselectivity. A unique Lewis acid induced fragmentation of these ten‐membered heterocycles was also discovered.

中文翻译:

Pd催化的乙烯基氧杂环丁烷与氮杂二烯的对映选择性[6 + 4]环加成反应,从而获得十元杂环。

我们在此报告了乙烯基氧杂环丁烷的第一个对映选择性环加成反应,其与氮杂二烯的反应通过[6 + 4]环加成反应提供了前所未有的十元杂环访问途径。通过使用市售的手性Pd-SIPHOX催化剂,可以以优异的收率和对映选择性获得各种苯并呋喃以及吲哚稠合的杂环。还发现了独特的路易斯酸诱导的这些十元杂环的断裂。
更新日期:2018-01-15
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