Nonclassical CH-π supramolecular interactions in artemisinic acid favor a single conformation, yielding high diastereoselectivity in the reduction with diazene

Journal of Organic Chemistry

Volumn 79, Issue 13, 2014, Pages 5939-5947

  Castro, Bertrand ^a   Chaudret, Robin ^b   Ricci, Gino ^c   Kurz, Michael ^d   Ochsenbein, Philippe ^c   Kretzschmar, Gerhard ^d   Kraft, Volker ^d   Rossen, Kai ^d   Eisenstein, Odile ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b IFP ENERGIES NOUVELLES   (France)

^c SANOFI   (France)

^d SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGENATION; IONS; LOW POWER ELECTRONICS;

ARTEMISINIC ACID; DFT CALCULATION; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; ELECTRON DONORS; NON-COVALENT INTERACTION; SUPRAMOLECULAR INTERACTIONS; TRANSITION STATE;

STEREOSELECTIVITY;

ARTEMISINIC ACID; DIHYDROARTEMISININ DERIVATIVE; EXOCYCLIC DOUBLE BOND; ARTEMISININ DERIVATIVE; DIAZENE; IMIDE; OXYGEN;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONFORMATION; CRYSTALLIZATION; DECOMPOSITION; DENSITY GRADIENT; DIASTEREOISOMER; ELECTRON TRANSPORT; GEOMETRY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HYDROGENATION; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; REDUCTION; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; CHEMISTRY; HYDROGEN BOND; STEREOISOMERISM;

ARTEMISININS; HYDROGEN BONDING; IMIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; OXYGEN; STEREOISOMERISM;

EID: 84903695988     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500233z     Document Type: Article

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