Anise Essential Oil as a Sustainable Substrate in the Multicomponent Double Povarov Reaction for Julolidine Synthesis

The use of star anise oil from a natural source as a dienophile in the multicomponent double Povarov reaction (MCPRs) to produce highly substituted julolidines with diverse technological applications is described. Within the framework of green chemistry, these MCPRs have many advantages such as (i)...

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Published inJournal of organic chemistry Vol. 85; no. 23; pp. 15622 - 15630
Main Authors Braga, Ingredy Bastos, Castañeda, Sandra Milena Bonilla, Vitor de Assis, João, Barros, Amanda Oliveira, Amarante, Giovanni Wilson, Valdo, Ana Karoline Silva Mendanha, Martins, Felipe Terra, Rosolen, Amanda Francisca do Prado, Pilau, Eduardo, Fernandes, Sergio Antonio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.12.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
CATALYSIS
3-COMPONENT
MICROWAVE-ASSISTED SYNTHESIS
ONE-POT
DIELS-ALDER REACTION
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Abstract The use of star anise oil from a natural source as a dienophile in the multicomponent double Povarov reaction (MCPRs) to produce highly substituted julolidines with diverse technological applications is described. Within the framework of green chemistry, these MCPRs have many advantages such as (i) use of water in the reaction, (ii) creation of up to six bonds in one sequence, (iii) water as a sole waste, (iv) 100% of carbon economy, (v) a metal-free process, and (vi) nontoxic and reusable organocatalysts. These advantages, along with a simple workup procedure, make this protocol greener for the synthesis of julolidines.
AbstractList The use of star anise oil from a natural source as a dienophile in the multicomponent double Povarov reaction (MCPRs) to produce highly substituted julolidines with diverse technological applications is described. Within the framework of green chemistry, these MCPRs have many advantages such as (i) use of water in the reaction, (ii) creation of up to six bonds in one sequence, (iii) water as a sole waste, (iv) 100% of carbon economy, (v) a metal-free process, and (vi) nontoxic and reusable organocatalysts. These advantages, along with a simple workup procedure, make this protocol greener for the synthesis of julolidines.
Author Amarante, Giovanni Wilson
Fernandes, Sergio Antonio
Valdo, Ana Karoline Silva Mendanha
Pilau, Eduardo
Barros, Amanda Oliveira
Braga, Ingredy Bastos
Castañeda, Sandra Milena Bonilla
Martins, Felipe Terra
Rosolen, Amanda Francisca do Prado
Vitor de Assis, João
AuthorAffiliation Instituto de Química
Grupo de Química Supramolecular e Biomimética (GQSB), Departamento de Química, CCE
Laboratório de Biomoléculas e Espectrometria de Massas, Departamento de Química
Departamento de Química
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Snippet The use of star anise oil from a natural source as a dienophile in the multicomponent double Povarov reaction (MCPRs) to produce highly substituted julolidines...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Anise Essential Oil as a Sustainable Substrate in the Multicomponent Double Povarov Reaction for Julolidine Synthesis
URI http://dx.doi.org/10.1021/acs.joc.0c02459
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