Diastereoselective Synthesis of 2-Arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via FeCl3路6H2O-Catalyzed Spiroannulation/Hydride Transfer of 6-(5-Arylpent-4-yn-1-yl)-7-oxabicyclo[

详细信息    查看全文

• 作者：Hsin-Hui Lin ; Kuan-Yi Lee ; Yin-An Chen ; Chi-Fan Liu ; Ming-Chang P. Yeh
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：December 5, 2014
• 年：2014
• 卷：79
• 期：23
• 页码：11802-11811
• 全文大小：432K
• ISSN：1520-6904

文摘

In the presence of a catalytic amount of FeCl₃路6H₂O, 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols underwent attack of the pendant acetylene at the iron-activated oxirane to give a vinylic carbocation. Hydride transfer from the carbinol carbon to the newly formed cation center furnished 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones in excellent stereoselectivity and good yields.