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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 |
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| Authors: | Albert S. C. Chan Chi-Ching LinJian Sun Wenhao Hu Zhi Li Weidong Pan Aiqiao Mi Yaozhong JiangTsang-Miao Huang Teng-Kuei Yang Jyh-Horung ChenYu WangGene-Hsiang Lee |
| Affiliation: | Union Laboratory of Asymmetric Synthesis. Department of Applied Biology and Chemical Technology, the Hong Kong Polytechnic University, Hong Kong Union Laboratory of Asymmetric Synthesis. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China Union Laboratory of Asymmetric Synthesis. Department of Chemistry, National Chung Hsing University, Taichung, Taiwan Department of Chemistry, National Taiwan University, Taipei, Taiwan |
| 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. |
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