Ruthenium carbene complexes with imidazol-2-ylidene ligands:: Syntheses of conduritol derivatives reveals superior RCM activity

被引:93
作者
Ackermann, L [1 ]
El Tom, D [1 ]
Fürstner, A [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
ruthenium carbene complex; olefination; metathesis;
D O I
10.1016/S0040-4020(99)01102-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of conduritol A, E and F derivatives are described using galactitol, D-mannitol and D-glucitol, respectively, as the starting materials. The key steps of this approach comprise a Tebbe olefination reaction for the preparation of dienes 15, 21 and 27 followed by ring closing metathesis (RCM) for the formation of the polyhydroxylated cyclohexene rings of the targets. A comparative study shows that the latter transformation is best achieved with catalytic amounts of ruthenium carbene complex 3a bearing one PCy3 and one 2,3-dihydro-1H-imidazol-2-ylidene ligand in its coordination sphere. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2195 / 2202
页数:8
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