Premium
Pd‐Catalyzed Enantioselective [6+4] Cycloaddition of Vinyl Oxetanes with Azadienes to Access Ten‐Membered Heterocycles
Author(s) -
Wang Yag,
Yang LiCheng,
Rong ZiQiang,
Liu TangLin,
Liu Ruoyang,
Zhao Yu
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711648
Subject(s) - cycloaddition , enantioselective synthesis , catalysis , benzofuran , indole test , chemistry , combinatorial chemistry , yield (engineering) , lewis acids and bases , organic chemistry , materials science , metallurgy
Abstract 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.