Litcius/Paper detail

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

Ingredy Bastos Braga, Sandra Milena Bonilla Castañeda, João Vítor de Assis, Amanda Oliveira Barros, Giovanni W. Amarante, Ana Karoline Silva Mendanha Valdo, Felipe Terra Martins, Amanda Francisca do Prado Rosolen, Eduardo Jorge Pilau, Sérgio Antônio Fernandes

2020The Journal of Organic Chemistry23 citationsDOI

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.

Topics & Concepts

ChemistrySubstrate (aquarium)Green chemistryOrganic chemistryAtom economyDouble bondAlkaneCarbon chainReaction mechanismCombinatorial chemistryHydrocarbonCatalysisOceanographyGeologyChemical Synthesis and ReactionsMulticomponent Synthesis of HeterocyclesAsymmetric Synthesis and Catalysis