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

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...

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Veröffentlicht in:Journal of the American Chemical Society 2012-10, Vol.134 (42), p.17564-17573
Hauptverfasser: Zheng, Ke, Liu, Xiaohua, Qin, Song, Xie, Mingsheng, Lin, Lili, Hu, Changwei, Feng, Xiaoming
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Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3062002