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Highly Enantioselective Construction of Tricyclic Derivatives by the Desymmetrization of Cyclohexadienones
Author(s) -
MartínSantos Cecilia,
JaravaBarrera Carlos,
del Pozo Sandra,
Parra Alejandro,
DíazTendero Sergio,
MasBallesté Rubén,
Cabrera Silvia,
Alemán José
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402853
Subject(s) - desymmetrization , tricyclic , enantioselective synthesis , chemistry , cycloaddition , aromaticity , density functional theory , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , catalysis , molecule
The asymmetric synthesis of tricyclic compounds by the desymmetrization of cyclohexadienones is presented. The reaction tolerated a large variety of substituents at different positions of the cyclohexadienone, and heterocyclic rings of different sizes were accessible. Density functional theory calculations showed that the reaction proceeds through an asynchronous [4+2] cycloaddition.
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