Total selective synthesis of enantiopure O1-acyl-3-aminoalkane-1,2-diols by ring opening of aminoepoxides with carboxylic acids

被引：13

作者：

Concellón, JM ^{[1
]}

Suárez, JR ^{[1
]}

del Solar, V ^{[1
]}

Llavona, R ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, Oviedo 33071, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期

关键词：

D O I：

10.1021/jo0514873

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of (2R,3S)- or (2S,3S)-O-1-acyl-3-aminoalkane-1,2-diols by ring opening of enantiopure (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides 1 or 2, with carboxylic acids in the presence of BF3-Et2O and chlorotrimethylsilane, is described. The conversion takes place with total selectivity and in good yield. In addition, (2R,3S)-O,O-diacyl-3-aminoalkane-1,2-diols 3 were also prepared from reaction of (2R, 1'S)-2-(1-aminoalkyl)epoxides 1 with carboxylic acids under the same reaction conditions and without chlorotrimethylsilane. Mechanisms to explain both transformations are proposed.

引用

页码：10348 / 10353

页数：6

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