Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides

Alex Zea; Guillem Valero; Andrea Nekane R. Alba; Albert Moyano; Ramon Rios

doi:10.1002/adsc.201000031

Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides

Alex Zea, Guillem Valero, Andrea Nekane R. Alba, Albert Moyano, Ramon Rios

Chemistry

Universitat de Barcelona

Research output: Contribution to journal › Article › peer-review

52 Scopus citations

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 DielsAlder or Michael adducts in excellent yields and enantioselectivities.

Original language	British English
Pages (from-to)	1102-1106
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	352
Issue number	7
DOIs	https://doi.org/10.1002/adsc.201000031
State	Published - 3 May 2010

Keywords

Anthrones
Diels-alder cycloaddition
Enantioselective
Maleimides
Michael addition
Organocatalysis

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10.1002/adsc.201000031

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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 DielsAlder or Michael adducts in excellent yields and enantioselectivities.",

keywords = "Anthrones, Diels-alder cycloaddition, Enantioselective, Maleimides, Michael addition, Organocatalysis",

author = "Alex Zea and Guillem Valero and Alba, {Andrea Nekane R.} and Albert Moyano and Ramon Rios",

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T1 - Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides

AU - Zea, Alex

AU - Valero, Guillem

AU - Alba, Andrea Nekane R.

AU - Moyano, Albert

AU - Rios, Ramon

PY - 2010/5/3

Y1 - 2010/5/3

N2 - 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 DielsAlder or Michael adducts in excellent yields and enantioselectivities.

AB - 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 DielsAlder or Michael adducts in excellent yields and enantioselectivities.

KW - Anthrones

KW - Diels-alder cycloaddition

KW - Enantioselective

KW - Maleimides

KW - Michael addition

KW - Organocatalysis

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U2 - 10.1002/adsc.201000031

DO - 10.1002/adsc.201000031

M3 - Article

AN - SCOPUS:77952189791

SN - 1615-4150

VL - 352

SP - 1102

EP - 1106

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 7

ER -

Bifunctional thiourea-catalyzed asymmetric addition of anthrones to maleimides

Abstract

Keywords

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