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
Resource
Tetrahedron: Asymmetry 6 (12): 2953-2959
Journal
Tetrahedron Asymmetry
Pages
2953-2959
Date Issued
1995
Date
1995
Author(s)
Chan, Albert S. C.
Lin, Chi-Ching
Sun, Jian
Hu, Wenhao
Li, Zhi
Pan, Weidong
Mi, Aiqiao
Jiang, Yaozhong
Huang, Tsang-Miao
Yang, Teng-Kuei
Chen, Jyh-Horung
Wang, Yu
Lee, Gene-Hsiang
Abstract
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 X-ray crystallography. © 1995.
Type
journal article
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