1353637-87-2Relevant articles and documents
An efficient route to highly enantioenriched tetrahydroazulenes and β-tetralones by desymmetrization reactions of δ,δ-diaryldiazoaceto-acetates
Liu, Yuxiao,Deng, Yongming,Zavalij, Peter Y.,Liu, Renhua,Doyle, Michael P.
, p. 565 - 568 (2015)
A highly stereoselective desymmetrization reaction of δ,δ-diaryl-α-diazo-β-ketoesters catalyzed by chiral dirhodium carboxylates forms aromatic cycloaddition products in up to 97% ee. This journal is
Construction of tetralin skeletons based on rhodium-catalysed site-selective ring opening of benzocyclobutenols
Ishida, Naoki,Ishikawa, Norikazu,Sawano, Shota,Masuda, Yusuke,Murakami, Masahiro
supporting information, p. 1882 - 1885 (2015/01/30)
Tetralins (tetrahydronaphthalenes) are synthesised from benzocyclobutenols based on the rhodium-catalysed site-selective ring opening followed by intermolecular/intramolecular conjugate addition of the resulting arylrhodium species to electron-deficient alkenes. The produced structures make a remarkable contrast with those available from the same compounds under thermal reaction conditions.
Synthesis and configuration determination of all enantiopure stereoisomers of the melatonin receptor ligand 4-phenyl-2-propionamidotetralin using an expedient optical resolution of 4-phenyl-2-tetralone
Lucarini, Simone,Bartolucci, Silvia,Bedini, Annalida,Gatti, Giuseppe,Orlando, Pierfrancesco,Piersanti, Giovanni,Spadoni, Gilberto
experimental part, p. 305 - 313 (2012/02/02)
An efficient and practical approach for the synthesis of all four stereoisomers of the MT2 melatonin receptor ligand 4-phenyl-2-propionamidotetralin (4-P-PDOT), each in enantiomerically pure form (ee > 99.9%), was developed. The strategy involved an optical resolution procedure of the key precursor (±)-4-phenyl-2-tetralone with the unusual resolving agent (S)-mandelamide, through the formation of four dihydronaphtalene-spiro-oxazolidin-4-one diastereomers. Interestingly, NMR experimental observations in combination with geometric calculations, provided unambiguous configuration assignments of all stereocenters of the key spiro stereoisomers. Cleavage of each single spiro diastereomer under acidic conditions gave enantiopure (R)- or (S)-4-phenyl-2-tetralone, which were then converted to each 4-P-PDOT single enantiomer by using stereoselective reactions.
