Synthesis of novel α-aminophosphonates by methanesulfonic acid catalyzed Kabachnik-Fields reaction

被引：6

作者：

Ravi, Nuchu ^{[1
,2
]}

Venkatanarayana, Muvvala ^{[1
]}

Sharathbabu, Haridasyam ^{[1
]}

Babu, Kilaru Ravendra ^{[2
]}

机构：

[1] GITAM, GITAM Sch Sci, Dept Chem, Hyderabad, India

[2] Mylan Labs Ltd, ANRICH Ind Estate, CRD, Hyderabad, India

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2021年 / 196卷 / 11期

关键词：

Fluoro amines; alpha-aminophosphonate; CH3SO3H; catalysis; enantioselectivity; ONE-POT SYNTHESIS; 3-COMPONENT SYNTHESIS; AMINO PHOSPHONATES; ALDEHYDES; FLUORINE; DERIVATIVES; INHIBITORS; MECHANISM; ANALOGS;

D O I：

10.1080/10426507.2021.1960834

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of novel alpha-aminophosphonates of diethyl (2,4-difluorobenzylamino)methylphosphonate derivatives (4a-4g) have been synthesized by applying three-component Kabachnik-Fields reaction, using fluoro derivatives of aldehydes and substituted amines, diethyl phosphonate in the presence of a catalytic amount of methanesulfonic acid (MSA) in good yields with high enantioselectivities (up to 98% ee). The enantioselectivitiy of compounds (4a-4g) was confirmed by chiral HPLC. The direct Kabachnik-Fields reaction with high reactivity under mild reaction conditions and significantly used for synthesis of the alpha-aminophosphonate. The novel products were characterized by spectral and analytical data. [GRAPHICS] .

引用

页码：1018 / 1024

页数：7

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