1952年， M. I. Kabachinik等人报道了三组分合成α-胺基膦酸的反应。酸催化下，伯胺或仲胺，醛酮和亚膦酸二烷基酯进行三组分反应得到α-胺基膦酸。底物除了亚膦酸二烷基酯，亚膦酸和膦酸三烷基酯也能进行此反应。常见的催化剂有，三氟甲磺酸的镧系金属盐(Sc, Yb, Sm, In)或Al, Co, Ni的酞菁络合物。

反应机理

反应实例

Diethyl aminophosphonate (4). To a solution of anhyd Yb(OTf)3 (0.0025 mmol) in 1 mL of ionic liq bmim-PF6 (N-butyl-N-Me-imidazolium salt) at r.t. was added aniline 2 (23.2 mg, 0.25 mmol) followed by 27 mg of PhCHO 1 (0.25 mmol) and diethyl phosphite 3 (138 mg, 1 mmol) with stirring. After 27 h repeated extraction with PhH and chromatography afforded 47 mg of 4, 95%. Yb catalyst can be reused.

【Lee S-gi， Chem Comm， 2001， 1698】

相关文献

1 Field EM J Am Chem Soc 1952 74 1528

2 Kabachnik MJ Dokl Akad Nauk SSSR 1952 689

3 Kabachnik MJ Izvest Akad Nauk SSSR (C) 1954 1024

4 Mo¨drizer K J Org Chem 1966 31 1603

5R Kuchar VP Russ Chem Rev 1987 56 1504

6 Kobayashi S Chem Comm 2000 669

7 Lee S-gi Chem Comm 2001 1698

8 Hanson PR J Org Chem 2002 67 8123

9 Zefirov NS Synlett 2003 2321

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 245.