Orthosilicate-mediated esterification of monosubstituted phosphinic acids

被引:49
作者
Dumond, YR [1 ]
Baker, RL [1 ]
Montchamp, JL [1 ]
机构
[1] Texas Christian Univ, Dept Chem, Ft Worth, TX 76129 USA
关键词
D O I
10.1021/ol006434g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Monosubstituted phosphinic acids are esterified with orthosilicates in excellent yields. Phosphinylidene-containing acids react selectively under these conditions, while disubstituted phosphinic acids and phosphonic acids remain unchanged. One-pot procedures are also described for the preparation of phosphinate esters from an alcohol. This novel method provides a convenient and general alternative to more commonly employed conditions such as diazomethane or carbodiimide.
引用
收藏
页码:3341 / 3344
页数:4
相关论文
共 36 条
[1]   New (α-hydroxyalkyl)phosphorus amphiphiles:: Synthesis and dissociation constants [J].
Albouy, D ;
Brun, A ;
Munoz, A ;
Etemad-Moghadam, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7223-7230
[2]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[3]   SYNTHESIS OF POTENTIAL INHIBITORS OF THE ENZYME PANTOTHENATE SYNTHETASE [J].
BAILLIE, AC ;
CORNELL, CL ;
WRIGHT, BJ ;
WRIGHT, K .
TETRAHEDRON LETTERS, 1992, 33 (35) :5133-5136
[4]   1,1-Diethoxyethylphosphinates and phosphonites. Intermediates for the synthesis of functional phosphorus acids [J].
Baylis, EK .
TETRAHEDRON LETTERS, 1995, 36 (51) :9385-9388
[5]   SYNTHESIS OF MYOINOSITOL 1-PHOSPHATE AND 4-PHOSPHATE, AND OF THEIR INDIVIDUAL ENANTIOMERS [J].
BILLINGTON, DC ;
BAKER, R ;
KULAGOWSKI, JJ ;
MAWER, IM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (04) :314-316
[6]   Investigations on new strategies for the facile synthesis of polyfunctionalized phosphinates: Phosphinopeptide analogues of glutathionylspermidine [J].
Chen, SJ ;
Coward, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :502-509
[7]  
Chen SJ, 1997, BIOORG MED CHEM LETT, V7, P505
[8]   RECHERCHES SUR LA FORMATION ET LA TRANSFORMATION DES ESTERS .47. SUR LES MONOESTERS DE DIVERS ACIDES DU PHOSPHORE ET SUR LEUR VITESSE DE SCISSION A DIFFERENTS PH [J].
CHERBULIEZ, E ;
RABINOWICZ, J ;
WEBER, G .
HELVETICA CHIMICA ACTA, 1963, 46 (06) :2464-&
[9]  
DUMOND YR, UNPUB
[10]  
ELEPINA LT, 1973, J GEN CHEM USSR, V43, P1795