ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .62. 1ST CARBENE COMPLEXES (M = CR, W) WITH CARBOHYDRATE SUBSTITUENTS

被引：42

作者：

AUMANN, R

机构：

[1] Organisch-Chemisches Institut, Universität Münster, Münster, W-4400

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 12期

关键词：

CARBENE COMPLEXES OF CARBOHYDRATE DERIVATIVES; VINYLCARBENE CHROMIUM AND TUNGSTEN COMPLEXES; DELTA-D-MANNOFURANOSIDES, 2,3-5,6-DI-O-ISOPROPYLIDENEFURANOSIDES, OF CARBENE COMPLEXES; ALPHA-D-ALLOFURANOSIDES, 1,2-5,6-DI-O-ISOPROPYLIDENEFURRANOSIDES, OF CARBENE COMPLEXES; ALPHA-D-GLUCOFURANOSIDES, 1,2-5,6-DI-O-ISOPROPYLIDENESFURANOSIDES, OF CARBENE COMPLEXES; 1,2-PROPADIENYLIDEN TUNGSTEN COMPLEX;

D O I：

10.1002/cber.19921251224

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of transition metal carbene complexes of carbohydrate derivatives are described: 1,2:5,6-Di-0-isopropyliden-alpha-D-glucofuranose (2a), 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose (2b), and 2,3:5,6-di-0-isopropyliden-alpha-D-mannofuranose (2c) add regiospecifically at C-3 of alkynylcarbene complexes L(n) = C(OEt) - C = CPh 1 [L(n)M = Cr(CO)5 (a), W(CO)5 (b)] to give vinylcarbene complexes L(n)M = C(OEt) - CH = C(Ph) - O(sugar) (E/Z)-3a-g in good to excellent yields. As a minor side reaction the alkynyl carbene complex (CO)5W = C(OEt) - C = CPh (1 b) isomerises to give the 1,2-propadienylidene complex (CO)5W = C = C = C(OEt)C6H5 (4 b).

引用

页码：2773 / 2778

页数：6