Premium
Thermal Intramolecular [2+2] Cycloaddition of Allenenes and Allenynes: Diastereoselective Access to Bicyclic Nitrogen Heterocycles
Author(s) -
Ohno Hiroaki,
Mizutani Tsuyoshi,
Kadoh Yoichi,
Miyamura Kumiko,
Tanaka Tetsuaki
Publication year - 2005
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.200501413
Subject(s) - cycloaddition , intramolecular force , bicyclic molecule , regioselectivity , octane , chemistry , adduct , nitrogen , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Squaring the circle : A route to bicyclo[4.2.0]octane derivatives has been developed by the [2+2] cycloaddition of allenenes or allenynes. The thermal intramolecular [2+2] cycloaddition of simple allenes 1 with an additional multiple bond leads to direct and regioselective formation of the distal adducts 2 in good to excellent yields.