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

TY - JOUR

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.

N1 - Copyright: Copyright 2004 Elsevier Science B.V., Amsterdam. All rights reserved.

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.

UR - https://www.scopus.com/pages/publications/0033574487

U2 - 10.1021/jo9823590

DO - 10.1021/jo9823590

M3 - Article

AN - SCOPUS:0033574487

SN - 0022-3263

VL - 64

SP - 2843

EP - 2846

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -