Premium
Synthesis and stereochemical analysis of some norephedrine‐derived isoxazolidines
Author(s) -
Moosa Basem A.,
Wazeer Mohamed I. M.,
Fettouhi Mohammed B.,
Ali Shaikh A.
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1454
Subject(s) - chemistry , cycloaddition , nmr spectra database , stereochemistry , solvent , nitrogen inversion , computational chemistry , organic chemistry , nitrogen , spectral line , catalysis , physics , astronomy
The diastereoselectivity in the cycloaddition reactions of several mono‐ and disubstituted alkenes with a (‐)norephedrine‐derived methylenenitrone has been investigated. The stereochemical analysis of the addition products (i.e., isoxazolidines) has been carried out by X‐ray, NMR, and chemical conversions. The NMR spectra of the isoxazolidines at low temperatures indicated the presence of either a single or a predominant invertomer. The stereochemistry of the invertomers and nitrogen inversion barriers are determined using complete line‐shape analysis and their dependence on solvent is discussed. Copyright © 2008 John Wiley & Sons, Ltd.