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

被引：22
作者：
Barluenga, J [1 ]
Baragaña, B [1 ]
Concellón, JM [1 ]
机构：
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Molesd, Oviedo 33071, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 08期
关键词：
D O I：
10.1021/jo9823590
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2-halomethyl-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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收藏
页码：2843 / 2846
页数：4
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