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001-es BibID:	BIBFORM001196
Első szerző:	Kerti Gábor (vegyész)
Cím:	Enantioselective synthesis of 3-methylisochromans and determination of their absolute configurations by circular dichroism / Gábor Kerti, Tibor Kurtán, Tünde-Zita Illyés, Katalin E. Kövér, Sándor Sólyom, Gennaro Pescitelli, Naoko Fujioka, Nina Berova, Sándor Antus
Dátum:	2007
Megjegyzések:	Seven (S)-3-methylisochromans with different substitution patterns on their aromatic rings, and hence with different directions of their sum electric transition moments, were synthesized by ring-closure of optically active (S)-1-arylpropan-2-ol derivatives. The (S)-1-arylpropan-2-ols were obtained by kinetic resolution and their absolute configurations were determined with the aid of a zinc porphyrin tweezer and by Mosher£s method. A systematic CD study of substituted isochroman derivatives revealed that, unlike in the cases of chiral tetralin and 2,3-dihydrobenzo[b]furan chromophores, the presence of achiral substituents of large spectroscopic moment (e.g., OMe) on the aromatic ring does not change the helicity rule of the Øunsubstitutedð isochroman chromophore: (P)/(M) helicity of the isochroman heteroring resulted in positive/negative 1Lb band Cotton effects (CE) regardless of the nature(s) and position(s) of the substituent(s). (S)-3-Methylisochromans were oxidized at C-1, allowing access to the corresponding dihydroisocoumarins, in which positive CE of the n-?* transitions were correlated with (P) helicity and (S) absolute configuration. On DDQ-assisted oxidation, two trans-1-methoxy-3-methylisochroman derivatives were prepared and used to study the effect of the axial benzylic C-1 methoxy group on the conformation of the heteroring and the 1Lb band CE.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban chirality configuration determination kinetic resolution
Megjelenés:	European Journal of Organic Chemistry. - 2 (2007), p. 296-305. -
További szerzők:	Kövér Katalin, E. (1956-2023) (vegyész) Sólyom Sándor Pescitelli, Gennaro (1972-) (vegyész) Fujioka, Naoko Berova, Nina Kurtán Tibor (1973-) (vegyész, angol szakfordító) Illyés Tünde Zita (1970-) (kémia-fizika szakos tanár) Antus Sándor (1944-2022) (vegyészmérnök)
Internet cím:	DOI elektronikus változat elektronikus változat
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