CsOH-promoted epoxide ring-opening with phosphines: mild and efficient synthesis of monohydroxyphosphines

被引：15

作者：

Fox, DL ^{[1
]}

Robinson, AA ^{[1
]}

Frank, JB ^{[1
]}

Salvatore, RN ^{[1
]}

机构：

[1] Western Kentucky Univ, Dept Chem, Bowling Green, KY 42101 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 41期

基金：

美国国家科学基金会;

关键词：

epoxides; phosphines; monohydroxyphosphine; cesium hydroxide; bidentate ligands;

D O I：

10.1016/j.tetlet.2003.08.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and convenient synthesis of monohydroxyphosphines has been achieved by epoxide ring-opening using primary or secondary phosphines in the presence of cesium hydroxide, 4 Angstrom molecular sieves and DMF at room temperature. These reaction conditions were found to be highly regio- and stereoselective producing various monohydroxyphosphines exclusively in moderate to high yields. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7579 / 7582

页数：4

共 34 条

[1] REACTION OF LITHIUM DIPHENYLPHOSPHIDE AND SIMPLE ARYL HALIDES [J].

AGUIAR, AM ;

RUBENSTEIN, KE ;

GREENBERG, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (08) :2091-&

[2] Copper(II) tetrafluoroborate catalyzed ring-opening reaction of epoxides with alcohols at room temperature [J].

Barluenga, J ;

Vázquez-Villa, H ;

Ballesteros, A ;

González, JM .

ORGANIC LETTERS, 2002, 4 (17) :2817-2819

[3] REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].

BONINI, C ;

RIGHI, G .

SYNTHESIS-STUTTGART, 1994, (03) :225-238

[4] Design and development of cyclohexane-based P,N-ligands for transition metal catalysis [J].

Caiazzo, A ;

Dalili, S ;

Yudin, AK .

ORGANIC LETTERS, 2002, 4 (15) :2597-2600

[5] REACTIONS OF TERTIARY DIPHOSPHINES WITH NICKEL AND NICKEL CARBONYL [J].

CHATT, J ;

HART, FA .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1378-1389

[6] Facile ring opening of oxiranes with aromatic amines in fluoro alcohols [J].

Das, U ;

Crousse, B ;

Kesavan, V ;

Bonnet-Delpon, D ;

Bégué, JP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6749-6751

[7] AN ASSESSMENT OF THE CAUSES OF THE CESIUM EFFECT [J].

DIJKSTRA, G ;

KRUIZINGA, WH ;

KELLOGG, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4230-4234

[8]

Erden I., 1996, COMPREHENSIVE HETE A, V1A, P97

[9]

FISHER C, 1977, TETRAHEDRON LETT, V18, P2487

[10] UNTERSUCHUNGEN DER KERNMAGNETISCHEN RESONANZ VON PHOSPHORVERBINDUNGEN .11. 31 P- KERNRESONANZDATEN DER ALKALI-DIPHENYLPHOSPHIDE [J].

FLUCK, E ;

ISSLEIB, K .

ZEITSCHRIFT FUR NATURFORSCHUNG PART B-CHEMIE BIOCHEMIE BIOPHYSIK BIOLOGIE UND VERWANDTEN GEBIETE, 1965, B 20 (11) :1123-&

← 1 2 3 4 →