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

doi:10.1021/jo9823590

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

Biological Chemistry and Drug Discovery

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2843-2846
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	64
Issue number	8
DOIs	https://doi.org/10.1021/jo9823590
Publication status	Published - 27 Mar 1999

ASJC Scopus subject areas

Organic Chemistry

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

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.",

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T1 - Preparation and synthetic applications of enantiopure (2S,3S)- or (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amines

AU - Barluenga, José

AU - Baragaña, Beatriz

AU - Concellón, José M.

PY - 1999/3/27

Y1 - 1999/3/27

N2 - 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.

AB - 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.

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

Abstract

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