Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol,Organic Letters

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Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol
Organic Letters ( IF 4.9 ) Pub Date : 2016-05-13 00:00:00 , DOI: 10.1021/acs.orglett.6b01047
Steven W. M. Crossley ₁ , Ruben M. Martinez ₁ , Sebastián Guevara-Zuluaga ₁ , Ryan A. Shenvi ₁

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Hydrogen atom transfer (HAT) circumvents a disfavored Friedel–Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.

中文翻译：

异戊二醇的自由基芳基化反应合成8-芳基醇类特权化合物

氢原子转移（HAT）避免了廉价的单萜异胡薄荷醇的衍生化中不利的Friedel-Crafts反应。各种易于制备的芳基和杂芳基磺酸盐经过正式的氢芳基化反应生成8-芳基薄荷醇，这是用于不对称合成的有优势的支架，以8-苯基薄荷醇为代表。在相关系统中观察到高立体选择性。HAT的这种使用极大地扩展了廉价的单萜异胡薄荷醇的手性库。

更新日期：2016-05-13

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