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Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides

Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides
Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides
For the first time, the addition of anthrones to maleimides catalyzed by bifunctional thiourea catalysts is reported. The thiourea moiety is able to activate the maleimide and the tertiary amine deprotonates the anthrone, furnishing the final Diels–Alder or Michael adducts in excellent yields and enantioselectivities.
anthrones, diels–alder cycloaddition, enantioselective, maleimides, michael addition, organocatalysis
1615-4150
1102-1106
Zea, Alex
e1cc8e2a-e3f2-46a2-8463-3015712bdb96
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Zea, Alex
e1cc8e2a-e3f2-46a2-8463-3015712bdb96
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Zea, Alex, Valero, Guillem, Alba, Andrea-Nekane R., Moyano, Albert and Rios, Ramon (2010) Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides. Advanced Synthesis & Catalysis, 352 (7), 1102-1106. (doi:10.1002/adsc.201000031).

Record type: Article

Abstract

For the first time, the addition of anthrones to maleimides catalyzed by bifunctional thiourea catalysts is reported. The thiourea moiety is able to activate the maleimide and the tertiary amine deprotonates the anthrone, furnishing the final Diels–Alder or Michael adducts in excellent yields and enantioselectivities.

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More information

e-pub ahead of print date: 28 April 2010
Published date: 3 May 2010
Keywords: anthrones, diels–alder cycloaddition, enantioselective, maleimides, michael addition, organocatalysis
Organisations: Chemistry
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Identifiers

Local EPrints ID: 347704
URI: http://eprints.soton.ac.uk/id/eprint/347704
DOI: doi:10.1002/adsc.201000031
ISSN: 1615-4150
PURE UUID: 1dfa612f-455d-4bda-afec-b2c33b340f60
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 11:38
Last modified: 14 Mar 2024 12:51

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Contributors

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

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