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Synthesis 2001(15): 2299-2306
DOI: 10.1055/s-2001-18447
DOI: 10.1055/s-2001-18447
PAPER
© Georg Thieme Verlag Stuttgart · New York
Lithiation of 2-(1-Chloroethyl)-2-oxazolines: Synthesis of Substituted Oxazolinyloxiranes and Oxazolinylaziridines
Further Information
Received
27 July 2001
Publication Date:
05 August 2004 (online)
Publication History
Publication Date:
05 August 2004 (online)
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
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