Mechanistic insight into the lanthanide (III) salt catalysed monoacylation of symmetrical diols from structural models

被引：20

作者：

Clarke, PA

Arnold, PL

Smith, MA

Natrajan, LS

Wilson, C

Chan, C

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoSmithKline, Med Chem, Stevenage SG1 2NY, Herts, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 20期

关键词：

D O I：

10.1039/b308171k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Model studies are presented that suggest the mechanism of the lanthanide(III) salt catalysed mono acylation of symmetrical diols proceeds via chelation of the diol and the anhydride to the lanthanide salt, followed by an 'intramolecular' acyl transfer.

引用

收藏

页码：2588 / 2589

页数：2

相关论文

共 14 条

[1] COMPLEXES OF CARBOHYDRATES WITH METAL-CATIONS .17. COMPLEX-FORMATION BETWEEN POLYOLS AND RARE-EARTH CATIONS - THE CRYSTAL-STRUCTURE OF GALACTITOL.2PRCL3.14 H2O [J].

ANGYAL, SJ ;

CRAIG, DC .

CARBOHYDRATE RESEARCH, 1993, 241 :1-8

[2]

Babler J. H., 1979, TETRAHEDRON LETT, V20, P1971

[3]

CHOUDARY BM, 1995, SYNLETT, P959

[4] A one-step procedure for the monoacylation of symmetrical 1,2-diols [J].

Clarke, PA ;

Kayaleh, NE ;

Smith, MA ;

Baker, JR ;

Bird, SJ ;

Chan, C .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5226-5231

[5] Selective mono-acylation of meso- and C2-symmetric 1,3-and 1,4-diols [J].

Clarke, PA .

TETRAHEDRON LETTERS, 2002, 43 (27) :4761-4763

[6] Direct one step mono-functionalisation of symmetrical 1,2-diols [J].

Clarke, PA ;

Holton, RA ;

Kayaleh, NE .

TETRAHEDRON LETTERS, 2000, 41 (15) :2687-2690

[7] Solid state and solution studies of lanthanide(III) complexes of cyclohexanetriols, models of the coordination sites found in sugars [J].

Delangle, P ;

Husson, C ;

Lebrun, C ;

Pécaut, J ;

Vottéro, PJA .

INORGANIC CHEMISTRY, 2001, 40 (13) :2953-2962

[8] Synthesis, structure, and solution studies of cyclohexantriol complexes of europium(III) [J].

Husson, C ;

Delangle, P ;

Pécaut, J ;

Vottéro, PJA .

INORGANIC CHEMISTRY, 1999, 38 (09) :2012-2019

[9] Desymmetrization of meso-1,2-diols via chiral Lewis acid-mediated ring-cleavage of 1,3-dioxolane derivatives [J].

Kinugasa, M ;

Harada, T ;

Oku, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :9067-9068

[10] C2-symmetric bis-sulfoxide:: A novel chiral auxiliary for asymmetric desymmetrization of cyclic meso-1,2-diols [J].

Maezaki, N ;

Sakamoto, A ;

Nagahashi, N ;

Soejima, M ;

Li, YX ;

Imamura, T ;

Kojima, N ;

Ohishi, H ;

Sakaguchi, K ;

Iwata, C ;

Tanaka, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3284-3291