Highly Enantioselective Construction of Tricyclic Derivatives by the Desymmetrization of Cyclohexadienones†
Cecilia Martín-Santos
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
These authors contributed equally.
Search for more papers by this authorCarlos Jarava-Barrera
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman
These authors contributed equally.
Search for more papers by this authorSandra del Pozo
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorDr. Alejandro Parra
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman
Search for more papers by this authorDr. Sergio Díaz-Tendero
Departamento de Química (Módulo 13), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorDr. Rubén Mas-Ballesté
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorDr. Silvia Cabrera
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorCorresponding Author
Dr. José Alemán
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman===Search for more papers by this authorCecilia Martín-Santos
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
These authors contributed equally.
Search for more papers by this authorCarlos Jarava-Barrera
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman
These authors contributed equally.
Search for more papers by this authorSandra del Pozo
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorDr. Alejandro Parra
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman
Search for more papers by this authorDr. Sergio Díaz-Tendero
Departamento de Química (Módulo 13), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorDr. Rubén Mas-Ballesté
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorDr. Silvia Cabrera
Departamento de Química Inorgánica (Módulo 7), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
Search for more papers by this authorCorresponding Author
Dr. José Alemán
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman
Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain) http://www.uam.es/jose.aleman===Search for more papers by this authorFinancial support from the Spanish Government (CTQ-2009-09431, CTQ-2012-12168, CTQ-2012-37420-C02-02) is gratefully acknowledged. J.A. and S.D.-T. thank the MICINN for their “Ramón y Cajal” contracts. A.P. thanks the MINECCO for a “Juan de la Cierva” contract. We gratefully acknowledge computational time provided by the CCC (UAM).
Abstract
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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