Lithiation of 2-(1-Chloroethyl)-2-oxazolines: Synthesis of Substituted Oxazolinyloxiranes and Oxazolinylaziridines

Vito Capriati; Leonardo Degennaro; Saverio Florio; Renzo Luisi; Carmela Tralli; Luigino Troisi

doi:10.1055/s-2001-18447

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Synthesis 2001(15): 2299-2306
DOI: 10.1055/s-2001-18447

PAPER

Lithiation of 2-(1-Chloroethyl)-2-oxazolines: Synthesis of Substituted Oxazolinyloxiranes and Oxazolinylaziridines

Vito Capriati^a, Leonardo Degennaro^a, Saverio Florio*^a, Renzo Luisi^a, Carmela Tralli^a, Luigino Troisi^b
^a Centro C.N.R. ”M.I.S.O.", Dipartimento Farmaco-Chimico, Università di Bari, Via E. Orabona 4, 70126 Bari, Italy
Fax: +39(080)5442231; e-Mail: florio@farmchim.uniba.it;
^b Dipartimento di Biologia, Università di Lecce, Via Monteroni, 73100 Lecce, Italy

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Publication History

Received 27 July 2001
Publication Date:
05 August 2004 (online)

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Abstract

Lithiation of 2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 2 leads to lithiated derivative 3, which is quite stable and can be deuterated, methylated and silylated to give oxazolines 4a-c. The reaction of 3 with carbonyl compounds and imines furnishes good to excellent yields of oxazolinylepoxides 6a-m and aziridines 17a-f, respectively. Methylation and NaBH₄ reduction of epoxides 6 afford oxazolidines 7 highly stereoselectively. Acylepoxides can be obtained by hydrolysis of the oxazolidine moiety.

Key words

oxazolinyloxiranes - oxazolinylaziridines - carbanion - nucleophilic addition

References

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1

Florio, S. unpublished results.