Synthesis of spiro[4.4]nonane-1,6-diols via the hydrogenation of spiro[4.4]nonane-1,6-dione: The profound effect of hydrogenating agents

被引：19
|
作者：
Chan, ASC
Lin, CC
Sun, J
Hu, WH
Li, Z
Pan, WD
Mi, AQ
Jiang, YZ
Huang, TM
Yang, TK
Chen, JH
Wang, Y
Lee, GH
机构：
[1] CHINESE ACAD SCI,CHENGDU INST ORGAN CHEM,CHENGDU,PEOPLES R CHINA
[2] NATL CHUNGHSING UNIV,DEPT CHEM,TAICHUNG 40227,TAIWAN
[3] NATL TAIWAN UNIV,DEPT CHEM,TAIPEI 10764,TAIWAN
来源：
TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 12期
关键词：
D O I：
10.1016/0957-4166(95)00392-4
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of spiro[4.4]nonane-1,6-diols via the catalytic as well as stoichiometric hydrogenation of spiro[4.4]nonane-1,6-dione was studied. Profound effects of the hydrogenation catalysts and reagents on the stereoselectivity of the products were observed. The choice of solvent also was found to have a significant influence on the product selectivity. The opening of a spiro-ring in the starting material was identified as a major side reaction in alcohol solvents. The absolute configuration of the trans,trans-diol was unambiguously determined by Xray crystallography.
引用
收藏
页码：2953 / 2959
页数：7
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