Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.
Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.
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DOI：
10.1021/acs.orglett.5b00972
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发表时间：
2015-05-01
期刊：
影响因子：
5.2
通讯作者：
Chain WJ
中科院分区：
文献类型：
--
作者：
Lewis RS;Garza CJ;Dang AT;Pedro TK;Chain WJ
报道了一种在无水氟化物作用下，由硅烷化前体在单个反应烧瓶中原位生成酮或酯烯醇化物和邻醌类化合物（o-QMs）的方案。在单个实验室操作中，将反应伙伴连接在一起得到多种β-（2-羟基苯基）羰基化合物，收率为32-94%。利用烯醇酸前体和传统卤代烃作为竞争烷基化剂的对照实验，以及分离不恢复芳香体系的偶联添加产生的1,5-二羰基产物，支持了o-QMs的中间性。
A protocol by which ketone or ester enolates and ortho-quinone methides (o-QMs) are generated in situ in a single reaction flask from silylated precursors under the action of anhydrous fluoride is reported. The reaction partners are joined to give a variety of β-(2-hydroxyphenyl)-carbonyl compounds in 32–94% yield in a single laboratory operation. The intermediacy of o-QMs is supported by control experiments utilizing enolate precursors and conventional alkyl halides as competitive alkylating agents and the isolation of 1,5-dicarbonyl products resulting from conjugate additions that do not restore the aromatic system.