Efficient one-pot synthesis of β-hydroxyphosphonates: regioselective nucleophilic ring opening reaction of epoxides with triethyl phosphite catalyzed by Al(OTf)3

Epihalohydrins in Organic Synthesis

“…Similarly, the reaction of epichlorohydrin ( 5 ) and epibromohydrin ( 6 ) with trialkyl phosphites and dialkyl phosphorochloridate in the presence of zinc(II) chloride afforded dialkyl 2-(dialkoxyphosphinyloxy)alkanephosphonates . Recently, the ring opening of epichlorohydrin ( 5 ) to β-hydroxyphosphonate ( 35 ) has been explored, catalyzed by Al(OTf) 3 as an efficient and reusable catalyst (Scheme ) . Among phosphonates, β-hydroxyphosphonates constitute an important class of compounds exhibiting useful biological properties leading to applications as herbicides, antibiotics, pesticides, antioxidants, and horticulture agents.…”

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

“…However, a simple and Scheme 12 Asymmetric addition to α-ketophosphonates to produce α-hydroxyphosphonates efficient synthesis of β-hydroxyphosphonate via opening of epoxides with phosphorus nucleophiles (phosphite triesters or H-phosphonate diesters) [83] was recently reported (Scheme 13). This reaction was recently extended to the synthesis of ribonucleoside 5 0 -β-hydroxyphosphonates by stereoselective opening of a chiral oxirane system in nucleoside derivatives with H-phosphonate diesters, in the presence of a silylating agent and BF 3 as a Lewis acid catalyst [84].…”

A new procedure for synthesis of $$\upalpha $$ α -aminophosphonates by aqueous formic acid as an effective and environment-friendly organocatalyst

“…20 Recently some new researches have been reported for promotion of one-pot Kabachnik-Fields reaction such as microwave irradiation, heating 21 and acidic or basic catalysts. Some Lewis acid catalysts, such as ZrOCl 2 • 5H 2 O, 22 Mg(ClO 4 ) 2 , 23 FeCl 3 , 24 Al(H 2 PO 4 ), 25 BiCl 3 , 26 InCl 3 , 27 YbCl 3 , 28 In(OTf) 3 , 29 Ce(OTf) 4 , 30 Fe 3 O 4 @ZrO 2 /SO 2− 4 , 31 CAN, 32 TaCl 5 SiO 2 , 33 SmI 2 , 34 LiClO 4 , 35 and some solid acids (montmorillonite KSF), silica sulphuric acid, and also some base catalysts like CaCl 2 , PPh 3 and other catalysts such as ZnO, TiO 2 , tosyl chloride and mesoporous aluminosilicate nanocage 36 have been used to succeed this reaction. In spite of all researches, still there are some serious limitations such as hard work up process, long reaction time and expensive and toxic catalyst in these methods.…”