Preparation and synthetic applications of enantiopure (2S,3S)- or (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amines

José Barluenga, Beatriz Baragaña, José M. Concellón

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2- halomethy-1-1,2-epoxyalkan-3-amine 4 have been obtained from 1-aminoalkyl halomethyl ketones 1 and (iodomethyl)lithium or (chloromethyl)lithium, respectively. Some synthetic applications of compounds 3 are described: chiral unsaturated 1,3-aminoalcohols 8 or 2-(halomethylidene)-3- (dibenzylamino)-alkan-1-ol 11 is obtained from 3 by halogeno-lithium or by hydrogen-lithium exchange, respectively. Transformation of 8c into its methyl ester derivative 9c is also reported.

Original languageEnglish
Pages (from-to)2843-2846
Number of pages4
JournalJournal of Organic Chemistry
Volume64
Issue number8
DOIs
Publication statusPublished - 27 Mar 1999

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