Completely OH-Selective FeCl3-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans

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• 作者：Ke Zheng ; Xiaohua Liu ; Song Qin ; Mingsheng Xie ; Lili Lin ; Changwei Hu ; Xiaoming Feng
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：October 24, 2012
• 年：2012
• 卷：134
• 期：42
• 页码：17564-17573
• 全文大小：805K
• 年卷期：v.134,no.42(October 24, 2012)
• ISSN：1520-5126

文摘

The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl₃-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and ¹⁸O-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.