Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols

Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols

The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-dimethylphenyl in (1) and 2,4,6-trimethylphenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)...

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Bibliographic Details
Main Authors: Matthew R. Carbone, Garrick A. Centola, Adam Haas, Kevin P. McClelland, Michael D. Moskowitz, Angelo M. Verderame, Mikael S. Olezeski, Louis J. Papa, Stephanie C. M. Dorn, William W. Brennessel, Daniel J. Weix
Format: Article
Language:English
Published: International Union of Crystallography 2014-11-01
Series:Acta Crystallographica Section E
Subjects:
crystal structure
sulfinamide
diastereomer
amino alcohol
hydrogen bonding
NMR
column chromatography
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536814022570
Description
Summary:The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-dimethylphenyl in (1) and 2,4,6-trimethylphenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)° in (1) and by 44.65 (19)° in (2). In the crystal of (1), N—H...O=S and C—H...O=S hydrogen bonds link molecules, forming chains along [100], while in (2), similar hydrogen bonds link molecules into chains along [010]. The absolute structures of both compounds were determined by resonance scattering.
ISSN:1600-5368

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