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Chiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Cyclic Enethioureas as Dienophiles: Stereocontrolled Access to Enantioenriched Hexahydropyrroloquinolines
- Source :
- Chemistry-A European Journal, Chemistry-A European Journal, Wiley-VCH Verlag, 2012, 18 (19), pp.5869-73. ⟨10.1002/chem.201200523⟩
- Publication Year :
- 2012
- Publisher :
- Wiley, 2012.
-
Abstract
- International audience; Three become one: Phosphoric acid-catalyzed enantioselective three-component Povarov reactions of aldehydes, anilines, and endocyclic enethioureas have been developed. This process afforded hexahydropyrroloquinolines in high yields with excellent diastereo- and enantioselectivities. The presence of the thiourea functionality is crucial for the enantioselectivity of the reaction.
- Subjects :
- Quinoline Derivatives
Coupling Reactions
Povarov reaction
010402 general chemistry
01 natural sciences
Catalysis
Coupling reaction
enethioureas
chemistry.chemical_compound
chiral Bronsted acids
Combinatorial Chemistry Techniques
Organic chemistry
organocatalysis
Bronsted Acid
Phosphoric Acids
Pyrroles
Diels-Alder Reaction
(-)-Martinellic Acid
Phosphoric acid
Cyclization-Elimination Reaction
Diels–Alder reaction
Asymmetric Catalysis
Aldehydes
Aniline Compounds
Molecular Structure
multicomponent reactions
[CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry
Chemistry
Formal Total-Synthesis
Organic Chemistry
Thiourea
Enantioselective synthesis
Stereoisomerism
General Chemistry
0104 chemical sciences
RNA, Plant
Organocatalysis
Martinellic Acid
Bignoniaceae
Quinolines
Bond-Forming Reactions
Brønsted–Lowry acid–base theory
Subjects
Details
- ISSN :
- 09476539 and 15213765
- Volume :
- 18
- Database :
- OpenAIRE
- Journal :
- Chemistry - A European Journal
- Accession number :
- edsair.doi.dedup.....f40cd3d910ef9a24b50486768472e417