کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5279847 | 1385634 | 2005 | 5 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Cyclic chlorophosphites as scaffolds for the one-pot synthesis of α-aminophosphonates under solvent-free conditions Cyclic chlorophosphites as scaffolds for the one-pot synthesis of α-aminophosphonates under solvent-free conditions](/preview/png/5279847.png)
New α-aminophosphonates of the type (OCH2CMe2CH2O)P(O)CH(NHCO2R)(Râ²) [6a-i, 7a-e, and 8a-c] have been synthesized in high yields by a three-component reaction using (OCH2CMe2CH2O)PCl (3), benzamide (or urethane or benzyl carbamate), and an aldehyde without using any catalyst under solvent-free conditions. This route can be readily adapted for bis-aminophosphonates as well as optically active binaphthoxy α-aminophosphonates; it also tolerates the phenolic -OH group as shown by the synthesis of hydroxy functionalized aminophosphonates. Partial hydrolysis of compounds 7a-d leads to products in which the phosphorinane ring is cleaved first. Compounds (OCH2CMe2CH2O)P(O)CH[NHC(O)Ph](9-anthryl) (6f) and optically pure (R,S)-(â)-(C20H12O2)P(O)CH(NHCO2Et)(Ph) (14a) were characterized by X-ray crystallography.
New enantiomerically enriched and racemic α-aminophosphonates are obtained by a solvent-free, one-pot procedure.
Journal: Tetrahedron Letters - Volume 46, Issue 19, 9 May 2005, Pages 3347-3351