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[5+2] Cycloaddition of 2‐(2‐Aminoethyl)oxiranes with Alkynes via Epoxide Ring‐Opening: A Facile Access to Azepines
Author(s) -
Hu Chao,
Song RenJie,
Hu Ming,
Yang Yuan,
Li JinHeng,
Luo Shenglian
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201604679
Subject(s) - cycloaddition , epoxide , annulation , chemistry , ring (chemistry) , tandem , substrate (aquarium) , stereochemistry , combinatorial chemistry , selectivity , medicinal chemistry , catalysis , organic chemistry , materials science , biology , composite material , ecology
A new FeCl 3 and BF 3 ⋅OEt 2 co‐catalyzed tandem hetero‐[5+2] cycloaddition of 2‐(2‐aminoethyl)oxiranes with a wide range of alkynes, including terminal alkynes and alkyl‐substituted internal alkynes is presented. This is the first example of rapid and facile production of diverse 2,3‐dihydro‐1 H ‐azepines through a sequence of epoxide ring‐opening, annulation, and dehydroxylation with broad substrate scope and exquisite selectivity control.