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β-Functionalized and α,β-Difunctionalized Ketones from 1-Arylallylic Alcohols via Dipotassio α,β-Dianion Intermediates
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2022-11-29 , DOI: 10.1002/adsc.202201047
Rikuo Hayashi 1 , Kaori Ando 2 , Taro Udagawa 3 , Masahiro Sai 1
Affiliation  

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.

中文翻译:

1-芳基烯丙醇通过二钾 α,β-双阴离子中间体制备 β-官能化和 α,β-双官能化酮

本研究报道了在(三甲基甲硅烷基)甲基钾 (TMSCH 2 K)存在的情况下,从现成的 1-芳基烯丙醇合成多种 β-官能化酮。反应通过形成高度亲核的双钾 α,β-二价阴离子作为关键中间体,作为金属均烯醇化物等价物进行。该协议还允许使用两种不同的亲电子试剂一锅法合成 α,β-双官能化酮,从而证明其相对于其他涉及金属均烯醇化物的协议的合成优势。
更新日期:2022-11-29
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