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

页码：2953 / 2959

页数：7

共 13 条

[1] SYNTHESIS AND RESOLUTION OF THE ENANTIOMERIC TRANS,TRANS-SPIRO[5.5]UNDECANE-1,7-DIOLS AND DETERMINATION OF THEIR ABSOLUTE-CONFIGURATION - (S)-(-)-SPIRO[5.5]UNDECANE-1,7-DIONE [J].