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Asymmetric organocatalytic anthrone additions to activated alkenes

Asymmetric organocatalytic anthrone additions to activated alkenes
Asymmetric organocatalytic anthrone additions to activated alkenes
Asymmetric organocatalytic additions of anthrones to activated alkenes are discussed. The reaction between anthrone or dithranol and ?,?-unsaturated aldehydes is catalyzed by diphenylprolinol trimethylsilyl ether in toluene at ?40 °C, giving the Michael adducts with good yields and enantioselectivities. Bifunctional amino-thioureas efficiently catalyze the additions of anthrones to both nitroalkenes and maleimides, and high enantioselectivities can be achieved in both instances at room temperature. In the case of nitroalkenes, a Michael addition takes exclusively place. Anthrone generally gives Diels–Alder cycloadducts in the reaction with maleimides, while dithranol affords the Michael adducts. Transition state working models in which the bifunctional catalyst binds simultaneously to the alkene and to the anthrone enolate account for the stereochemical outcome of these additions.
anthrones, asymmetric catalysis, diels–alder cycloaddition, michael addition, organocatalysis
0040-4020
2513-2529
Zea, Alex
e1cc8e2a-e3f2-46a2-8463-3015712bdb96
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Bravo, Natalia
b4885173-6065-4fb7-accb-392f7d05735b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Zea, Alex
e1cc8e2a-e3f2-46a2-8463-3015712bdb96
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Bravo, Natalia
b4885173-6065-4fb7-accb-392f7d05735b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Zea, Alex, Alba, Andrea-Nekane R., Bravo, Natalia, Moyano, Albert and Rios, Ramon (2011) Asymmetric organocatalytic anthrone additions to activated alkenes. Tetrahedron, 67 (14), 2513-2529. (doi:10.1016/j.tet.2011.02.032).

Record type: Article

Abstract

Asymmetric organocatalytic additions of anthrones to activated alkenes are discussed. The reaction between anthrone or dithranol and ?,?-unsaturated aldehydes is catalyzed by diphenylprolinol trimethylsilyl ether in toluene at ?40 °C, giving the Michael adducts with good yields and enantioselectivities. Bifunctional amino-thioureas efficiently catalyze the additions of anthrones to both nitroalkenes and maleimides, and high enantioselectivities can be achieved in both instances at room temperature. In the case of nitroalkenes, a Michael addition takes exclusively place. Anthrone generally gives Diels–Alder cycloadducts in the reaction with maleimides, while dithranol affords the Michael adducts. Transition state working models in which the bifunctional catalyst binds simultaneously to the alkene and to the anthrone enolate account for the stereochemical outcome of these additions.

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More information

Published date: 8 April 2011
Keywords: anthrones, asymmetric catalysis, diels–alder cycloaddition, michael addition, organocatalysis
Organisations: Chemistry

Identifiers

Local EPrints ID: 347690
URI: http://eprints.soton.ac.uk/id/eprint/347690
ISSN: 0040-4020
PURE UUID: 09750192-bace-4972-a0fc-32ed02bffcda
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 10:33
Last modified: 15 Aug 2019 00:36

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Contributors

Author: Alex Zea
Author: Andrea-Nekane R. Alba
Author: Natalia Bravo
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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