Synthesis of α-hydroxy phosphonates using a solid supported base

被引:18
作者
Alexander, CW [1 ]
Albiniak, PA [1 ]
Gibson, LR [1 ]
机构
[1] Coll Charleston, Dept Chem & Biochem, Charleston, SC 29424 USA
基金
美国国家科学基金会;
关键词
alpha-hydroxy phosphonate; ion exchange resin; quaternary ammonium hydroxide; diethyl phosphite;
D O I
10.1080/10426500008082399
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A mild, efficient synthesis of alpha -hydroxy phosphonates is described where a quaternary ammonium hydroxide ion exchange resin is used as a base to promote the addition of diethyl phosphite to aryl aldehydes for a Pudikov type reaction.
引用
收藏
页码:205 / 209
页数:5
相关论文
共 29 条
[21]   AN UNEXPECTED REACTIVITY OF SIMPLE HETEROGENEOUS MIXTURE OF GAMMA-ALUMINA AND POTASSIUM FLUORIDE - 1-HYDROXYALKANE PHOSPHONIC ESTERS SYNTHESIS FROM NONACTIVATED KETONES IN DRY MEDIA [J].
TEXIERBOULLET, F ;
LEQUITTE, M .
TETRAHEDRON LETTERS, 1986, 27 (30) :3515-3516
[22]  
TEXIERBOULLET F, 1982, SYNTHESIS-STUTTGART, P916
[23]  
TEXIERBOULLET F, 1982, SYNTHESIS-STUTTGART, P165
[24]   The catalytic asymmetric aminohydroxylation of unsaturated phosphonates [J].
Thomas, AA ;
Sharpless, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8379-8385
[25]   ANIONIC ACTIVATION OF DIETHYLPHOSPHITE BY POTASSIUM FLUORIDE DEPOSITED ON ALUMINUM, SYNTHESIS OF FUNCTIONALIZED PHOSPHONATES [J].
VILLEMIN, D ;
RACHA, R .
TETRAHEDRON LETTERS, 1986, 27 (16) :1789-1790
[26]   An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acid by hydrolytic kinetic resolution of (±)-diethyl oxiranephosphonate [J].
Wyatt, PB ;
Blakskjær, P .
TETRAHEDRON LETTERS, 1999, 40 (35) :6481-6483
[27]  
YOKAMATSU T, 1997, J CHEM SOC P1, P1527
[28]   STEREODIVERGENT SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXYPHOSPHONIC ACID-DERIVATIVES BY LEWIS-ACID MEDIATED STEREOSELECTIVE HYDROPHOSPHONYLATION OF ALPHA-AMINO ALDEHYDES [J].
YOKOMATSU, T ;
YAMAGISHI, T ;
SHIBUYA, S .
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1401-1404
[29]   STEREOSELECTIVE SYNTHESIS OF BETA-OXYGENATED ALPHA-HYDROXYPHOSPHONATES BY LEWIS ACID-MEDIATED STEREOSELECTIVE HYDROPHOSPHONYLATION OF ALPHA-BENZYLOXY ALDEHYDES - AN APPLICATION TO THE SYNTHESIS OF PHOSPHONIC ACID ANALOGS OF OXYAMINO ACIDS [J].
YOKOMATSU, T ;
YOSHIDA, Y ;
SHIBUYA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7930-7933