1952年， M. I. Kabachinik等人報(bào)道了三組分合成α-胺基膦酸的反應(yīng)。酸催化下，伯胺或仲胺，醛酮和亞膦酸二烷基酯進(jìn)行三組分反應(yīng)得到α-胺基膦酸。底物除了亞膦酸二烷基酯，亞膦酸和膦酸三烷基酯也能進(jìn)行此反應(yīng)。常見(jiàn)的催化劑有，三氟甲磺酸的鑭系金屬鹽(Sc, Yb, Sm, In)或Al, Co, Ni的酞菁絡(luò)合物。
反應(yīng)機(jī)理
反應(yīng)實(shí)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】
相關(guān)文獻(xiàn)
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
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 245.
