CHIRAL BETA-AMINO SULFOXIDES - SYNTHESIS, CONFIGURATIONAL ASSIGNMENT AND CONFORMATIONAL-ANALYSIS BASED ON X-RAY, CD, H-1-NMR AND THEORETICAL CALCULATIONS

Authors
LEWANOWICZ A LIPINSKI J SIEDLECKA R SKARZEWSKI J BAERT F
Citation
A. Lewanowicz et al., CHIRAL BETA-AMINO SULFOXIDES - SYNTHESIS, CONFIGURATIONAL ASSIGNMENT AND CONFORMATIONAL-ANALYSIS BASED ON X-RAY, CD, H-1-NMR AND THEORETICAL CALCULATIONS, Tetrahedron, 54(23), 1998, pp. 6571-6586
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
23
Year of publication
1998
Pages
6571 - 6586
Database
ISI
SICI code
0040-4020(1998)54:23<6571:CBS-SC>2.0.ZU;2-U
Abstract
Enantiomerically pure u and l beta-amino sulfoxides have been easily o btained from the respective homochiral cr-amino alcohols. The absolute configuration at the created stereogenic centre was assigned by CD sp ectra and by X-ray analysis. Conformational analysis of the title comp ounds was carried out using quantum chemical energy-geometry optimizat ion. Thus established conformational behavior explained the strongly c onfiguration dependent NMR spectral patterns observed for the u and l diastereomers. (C) 1998 Elsevier Science Ltd. All rights reserved.