The first example of ring expansion of N-tosylaziridines to 2-aroyl-N-tosylazetidines with nitrogen ylides in an aqueous medium
Identifieur interne : 000F14 ( Main/Exploration ); précédent : 000F13; suivant : 000F15The first example of ring expansion of N-tosylaziridines to 2-aroyl-N-tosylazetidines with nitrogen ylides in an aqueous medium
Auteurs : Garima [Inde] ; Vishnu P. Srivastava [Inde] ; Lal Dhar S. Yadav [Inde]Source :
- Green Chemistry [ 1463-9262 ] ; 2010.
English descriptors
- Teeft :
- 2harom, Amine, Ammonium, Anal, Azetidination, Azetidine, Azetidines, Aziridine, Bromide, Calcd, Cdcl3, Chem, Eims, Green chem, Isomer, Lett, Mmol, Nitrogen ylides, Organic reactions, Phenacyl, Phenacyl bromide, Phenacyl bromide derivatives, Quaternary ammonium salt, Ring expansion, Royal society, Separate step, Silica, Silica system, Tertiary amine, Tetrahedron, Tetrahedron lett, Trans, Trans isomer, Umax, Yadav, Ylide.
Abstract
Tertiary amine catalyzed ring expansion reaction of N-tosylaziridines to 2-aroyl-N-tosylazetidines, with nitrogen ylides formed in situ from phenacyl bromide derivatives in a silica gel-water system is reported. The reaction expeditiously affords functionalized azetidines in high yields and stereoselectivities in a one-pot process. Advantageously, the protocol precludes the preparation and isolation of nitrogen ylides and their precursors in a separate step as they are formed in situ.
Url:
DOI: 10.1039/c004736h
Affiliations:
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Le document en format XML
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<term>Anal</term>
<term>Azetidination</term>
<term>Azetidine</term>
<term>Azetidines</term>
<term>Aziridine</term>
<term>Bromide</term>
<term>Calcd</term>
<term>Cdcl3</term>
<term>Chem</term>
<term>Eims</term>
<term>Green chem</term>
<term>Isomer</term>
<term>Lett</term>
<term>Mmol</term>
<term>Nitrogen ylides</term>
<term>Organic reactions</term>
<term>Phenacyl</term>
<term>Phenacyl bromide</term>
<term>Phenacyl bromide derivatives</term>
<term>Quaternary ammonium salt</term>
<term>Ring expansion</term>
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<term>Separate step</term>
<term>Silica</term>
<term>Silica system</term>
<term>Tertiary amine</term>
<term>Tetrahedron</term>
<term>Tetrahedron lett</term>
<term>Trans</term>
<term>Trans isomer</term>
<term>Umax</term>
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<front><div type="abstract">Tertiary amine catalyzed ring expansion reaction of N-tosylaziridines to 2-aroyl-N-tosylazetidines, with nitrogen ylides formed in situ from phenacyl bromide derivatives in a silica gel-water system is reported. The reaction expeditiously affords functionalized azetidines in high yields and stereoselectivities in a one-pot process. Advantageously, the protocol precludes the preparation and isolation of nitrogen ylides and their precursors in a separate step as they are formed in situ.</div>
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