NOVEL CONCEPTS IN DIRECTED BIARYL SYNTHESIS .40. SYNTHESIS, STRUCTURE, DYNAMICS AND 1ST ATROPISOMER-SELECTIVE CLEAVAGE OF THE CHROMIUM TRICARBONYL COMPLEX OF A LACTONE-BRIDGED BIARYL

被引:28
作者
BRINGMANN, G [1 ]
GOBEL, L [1 ]
PETERS, K [1 ]
PETERS, EM [1 ]
VONSCHNERING, HG [1 ]
机构
[1] MAX PLANCK INST FESTKORPERFORSCH,D-70506 STUTTGART,GERMANY
关键词
CRYSTAL STRUCTURES; CHROMIUM COMPLEXES; CARBONYL COMPLEXES; LACTONE COMPLEXES; STEREOSELECTIVE SYNTHESIS; ATROPISOMERISM; BRIDGED BIARYLS;
D O I
10.1016/0020-1693(94)03916-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The regioselective complexation of the unsymmetric lactone-type bridged biaryl 1 with a chromium tricarbonylfragment is reported. By temperature dependent NMR of the resulting complex 3, the activation barrier of the helix inversion was determined. This isomerization process is of fundamental importance for the atroposelective opening of the lactone bridge. In the crystal, by contrast, only one diastereomer exists, as determined by X-ray diffraction study. A first experiment on the stereoselective ring opening using the achiral H-nucleophile sodium borohydride leads to only one detectable atropo-diastereomer and demonstrates the great potential utility of chromium tricarbonyl complexes in directed biaryl synthesis and for mechanistic studies of the stereochemically intriguing lactone opening step.
引用
收藏
页码:255 / 260
页数:6
相关论文
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