Direct monoalkylation of alkyl phosphinates to access H-phosphinic acid esters

被引:19
作者
Abrunhosa-Thomas, I [1 ]
Ribière, P [1 ]
Adcock, AC [1 ]
Montchamp, JL [1 ]
机构
[1] Texas Christian Univ, Dept Chem, Ft Worth, TX 76129 USA
来源
SYNTHESIS-STUTTGART | 2006年 / 02期
关键词
phosphorus; H-phosphinic acid; phosphinates; alkylation; hypophosphite;
D O I
10.1055/s-2005-924768
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simple alkyl phosphinates prepared by the silicate esterification method can be alkylated under Barbier-like conditions with butyl lithium at -78 degrees C followed by warming to room temperature. The method is limited to the more reactive electrophile such as allylic bromides and alkyl iodides. With these electrophiles good yields of H-phosphinic acid esters are generally obtained in a straightforward manner.
引用
收藏
页码:325 / 331
页数:7
相关论文
共 50 条
[11]   A novel and convenient preparation of hypophosphite esters [J].
Deprèle, S ;
Montchamp, JL .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 :154-163
[12]   Palladium-catalyzed hydrophosphinylation of alkenes and alkynes [J].
Deprèle, S ;
Montchamp, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9386-9387
[13]   Triethylborane-initiated room temperature radical addition of hypophosphites to olefins:: Synthesis of monosubstituted phosphinic acids and esters [J].
Deprèle, S ;
Montchamp, JL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6745-6755
[14]  
DINGWALL JG, 1987, PHOSPHORUS SULFUR, V30, P571
[15]   DIETHOXYMETHYLPHOSPHONITES AND PHOSPHINATES - INTERMEDIATES FOR THE SYNTHESIS OF ALPHA-BETA-AMINOALKYLPHOSPHONOUS AND GAMMA-AMINOALKYLPHOSPHONOUS ACIDS [J].
DINGWALL, JG ;
EHRENFREUND, J ;
HALL, RG .
TETRAHEDRON, 1989, 45 (12) :3787-3808
[16]   ORGANOPHOSPHORUS INTERMEDIATES .6. BASE-CATALYZED REACTION OF METHYL PHOSPHINATE WITH TETRAPHENYLCYCLOPENTADIENONE [J].
FOOKES, CJR ;
GALLAGHER, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (19) :1876-1879
[17]   FORMATION OF ALKYL PHOSPHENITES FROM ALKYL PHOSPHINATES [J].
FOOKES, CJR ;
GALLAGHER, MJ ;
HONEGGER, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (07) :324-325
[18]   PHOSPHINIC ACID ANALOGS OF GABA .1. NEW POTENT AND SELECTIVE GABA(B) AGONISTS [J].
FROESTL, W ;
MICKEL, SJ ;
HALL, RG ;
VONSPRECHER, G ;
STRUB, D ;
BAUMANN, PA ;
BRUGGER, F ;
GENTSCH, C ;
JAEKEL, J ;
OLPE, HR ;
RIHS, G ;
VASSOUT, A ;
WALDMEIER, PC ;
BITTIGER, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (17) :3297-3312
[19]   PHOSPHINIC ACID ANALOGS OF GABA .2. SELECTIVE, ORALLY-ACTIVE GABA(B) ANTAGONISTS [J].
FROESTL, W ;
MICKEL, SJ ;
VONSPRECHER, G ;
DIEL, PJ ;
HALL, RG ;
MAIER, L ;
STRUB, D ;
MELILLO, V ;
BAUMANN, PA ;
BERNASCONI, R ;
GENTSCH, C ;
HAUSER, K ;
JAEKEL, J ;
KARLSSON, G ;
KLEBS, K ;
MAITRE, L ;
MARESCAUX, C ;
POZZA, MF ;
SCHMUTZ, M ;
STEINMANN, MW ;
VANRIEZEN, H ;
VASSOUT, A ;
MONDADORI, C ;
OLPE, HR ;
WALDMEIER, PC ;
BITTIGER, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (17) :3313-3331
[20]  
Galkin V. I., 1987, DOKL CHEM, V292, P21