β‐Functionalized and α,β‐Difunctionalized Ketones from 1‐Arylallylic Alcohols via Dipotassio α,β‐Dianion Intermediates
β‐Functionalized and α,β‐Difunctionalized Ketones from 1‐Arylallylic Alcohols via Dipotassio α,β‐Dianion Intermediates
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通过二钾 α,β-二价阴离子中间体从 1-芳基烯丙醇生成 β-官能化酮和 α,β-双官能化酮
DOI：
10.1002/adsc.202201047
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发表时间：
2023
影响因子：
5.4
通讯作者：
Sai Masahiro
中科院分区：
文献类型：
--
作者：
Hayashi Rikuo;Ando Kaori;Udagawa Taro;Sai Masahiro
本研究报道了在（三甲基硅基）甲基钾（TMSCH2K）存在下，由易得的1-芳烯醇合成多种β功能化酮。该反应通过形成高度亲核的二钾α， β-碘离子作为关键中间体，作为金属同质烯酸盐等价物进行。该方案还允许使用两种不同的亲电试剂一锅合成α， β-二功能化酮，从而证明了其合成优于其他涉及金属同源烯酸酯的方案。
This study reports the synthesis of diverse β-functionalized ketones from readily available 1-arylallylic alcohols in the presence of (trimethylsilyl) methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio α, β-dianion as the key intermediate, which served as a metal homoenolate equivalent. This protocol also allowed the one-pot synthesis of α, β-difunctionalized ketones using two different electrophiles, thus demonstrating its synthetic advantages over other protocols involving metal homoenolates.