HFIP Solvent Enables Alcohols To Act as Alkylating Agents in Stereoselective Heterocyclization,Journal of the American Chemical Society

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HFIP Solvent Enables Alcohols To Act as Alkylating Agents in Stereoselective Heterocyclization
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-04-12 , DOI: 10.1021/jacs.9b02198
Yuxiang Zhu ₁ , Ignacio Colomer ₁ , Amber L Thompson ₁ , Timothy J Donohoe ₁

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A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.

中文翻译：

HFIP 溶剂使醇能够在立体选择性杂环化中充当烷基化剂

提出了一种使用烯丙醇或苯甲醇作为烷化剂立体选择性合成高度官能化氧杂环的新方法。该过程高效且原子经济，产生的水是唯一的化学计量副产品。HFIP 溶剂中低于化学计量的 Ti(OiPr)4 是这种反应性的关键，并且该方法在醇引发剂和高烯丙醇底物上都可以容忍广泛的取代模式。初步的机理研究揭示了钛配合物与 HFIP 的原位形成，这可能会引发环化反应。产品的进一步立体选择性功能化允许获得各种有趣的杂环结构。

更新日期：2019-04-12

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