Synthesis and stereochemical analysis of some norephedrine-derived isoxazolidines

Basem A. Moosa; Mohamed I.M. Wazeer; Mohammed B. Fettouhi; Shaikh A. AIi

doi:10.1002/poc.1454

Synthesis and stereochemical analysis of some norephedrine-derived isoxazolidines

Basem A. Moosa, Mohamed I.M. Wazeer, Mohammed B. Fettouhi, Shaikh A. AIi

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	212-220
Number of pages	9
Journal	Journal of Physical Organic Chemistry
Volume	22
Issue number	3
DOIs	https://doi.org/10.1002/poc.1454
State	Published - Mar 2009
Externally published	Yes

Keywords

Asymmetric induction
Cycloaddition reactions
Inversion barriers
Invertomers
Isoxazoldines
Nitrogen inversion
Nitrone
Stereochemistry

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/poc.1454

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title = "Synthesis and stereochemical analysis of some norephedrine-derived isoxazolidines",

abstract = "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.",

keywords = "Asymmetric induction, Cycloaddition reactions, Inversion barriers, Invertomers, Isoxazoldines, Nitrogen inversion, Nitrone, Stereochemistry",

author = "Moosa, {Basem A.} and Wazeer, {Mohamed I.M.} and Fettouhi, {Mohammed B.} and AIi, {Shaikh A.}",

year = "2009",

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doi = "10.1002/poc.1454",

language = "English (US)",

volume = "22",

pages = "212--220",

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publisher = "John Wiley and Sons Ltd",

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T1 - Synthesis and stereochemical analysis of some norephedrine-derived isoxazolidines

AU - Moosa, Basem A.

AU - Wazeer, Mohamed I.M.

AU - Fettouhi, Mohammed B.

AU - AIi, Shaikh A.

PY - 2009/3

Y1 - 2009/3

N2 - 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.

AB - 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.

KW - Asymmetric induction

KW - Cycloaddition reactions

KW - Inversion barriers

KW - Invertomers

KW - Isoxazoldines

KW - Nitrogen inversion

KW - Nitrone

KW - Stereochemistry

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DO - 10.1002/poc.1454

M3 - Article

AN - SCOPUS:62549120814

SN - 0894-3230

VL - 22

SP - 212

EP - 220

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

IS - 3

ER -

Synthesis and stereochemical analysis of some norephedrine-derived isoxazolidines

Abstract

Keywords

ASJC Scopus subject areas

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