Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent

被引：69

作者：

El Kaïm, L ^{[1
]}

Gaultier, L ^{[1
]}

Grimaud, L ^{[1
]}

Dos Santos, A ^{[1
]}

机构：

[1] Ecole Natl Super Tech Avancees, Lab Chim Procedes, F-75739 Paris, France

来源：

SYNLETT | 2005年 / 15期

关键词：

Pudovik reaction; dialkylphosphite; phosphate esters; phospha-Brook rearrangement;

D O I：

10.1055/s-2005-872670

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate.

引用

页码：2335 / 2336

页数：2

共 15 条

[1] ABRUZOV BA, 1977, IAN SSSR KH, V9, P2156
[2] FLOYD AJ, 1970, TETRAHEDRON LETT, V20, P1735
[3] FOKIN AV, 1981, IZV AKAD NAUK SSSR S, V7, P1655
[4] ORGANOPHOSPHORUS INTERMEDIATES .2. REACTION OF TERVALENT PHOSPHORUS COMPOUNDS WITH TETRAPHENYLCYCLOPENTADIENONE
GALLAGHER, MJ
JENKINS, ID
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18): : 2605 - +
[5] KONOVALOVA IV, 1991, ZH OBSHCH KHIM, V61, P1018
[6] KRUTIKOV VI, 1986, ZH OBSHCH KHIM+, V56, P2027
[7] ALPHA-HYDROXY PHOSPHINYL-BASED INHIBITORS OF HUMAN RENIN
PATEL, DV
RIELLYGAUVIN, K
RYONO, DE
FREE, CA
ROGERS, WL
SMITH, SA
DEFORREST, JM
OEHL, RS
PETRILLO, EW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (22) : 4557 - 4569
[8] POLEZHAEVA NA, 1986, IZV NAUK SSSR SER KH, V8, P1860
[9] PUDOVIK AN, 1964, ZH OBSHCH KHIM+, V34, P2902
[10] PUDOVIK AN, 1979, SYNTHESIS-STUTTGART, P81

← 1 2 →