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Synlett 1991; 1991(5): 347-348
DOI: 10.1055/s-1991-34743
DOI: 10.1055/s-1991-34743
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Efficient Alkylation of Nitrogen Heterocycles Using Lithium Salts and Oxygen Leaving Groups
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Publikationsverlauf
Publikationsdatum:
07. März 2002 (online)
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Superior yields of N-alkylated nitrogen heterocycles have been achieved with remarkable regioselectivity. The lithium salt of the heterocycle was prepared by treatment with butyllithium in tetrahydrofuran. Reaction of this salt at room temperature with electrophiles, such as alkyl methanesulfonates and 1,2-epoxypropane, bearing an oxygen leaving group proceeded quantitatively and gave exclusive N-alkylation with no detectable C-alkylation.