Crosby Stuart R, Harding John R, King Clare D, Parker Gregory D, Willis Christine L
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
Org Lett. 2002 Feb 21;4(4):577-80. doi: 10.1021/ol0102850.
[reaction: see text] Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.
[反应：见正文] 本文给出了苄基高烯丙醇普林斯环化反应机理的证据，该证据表明反应结果取决于芳环上的取代基。富电子芳环的存在有利于氧杂环丙烷-科普重排，生成对称的四氢吡喃作为通过侧链交换过程形成的主要产物。相比之下，对于缺电子芳环，则形成预期的2,4,6-三取代四氢吡喃。
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