Thermal Intramolecular [2+2] Cycloaddition of Allenenes and Allenynes: Diastereoselective Access to Bicyclic Nitrogen Heterocycles | Zendy

Ohno Hiroaki | Zendy; Mizutani Tsuyoshi | Zendy; Kadoh Yoichi | Zendy; Miyamura Kumiko | Zendy; Tanaka Tetsuaki | Zendy

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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.

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