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Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal
Synlett ( IF 2 ) Pub Date : 2020-10-22 , DOI: 10.1055/s-0040-1706538
Hideki Yorimitsu 1 , Shuo Wang , Atsushi Kaga
Affiliation  

Sodium dispersion promotes reductive ring opening of arylcyclopropanes. The presence of a reduction-resistant electrophile, such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

中文翻译:

芳基环丙烷与金属钠的还原开环 1,3-双官能化

钠分散促进芳基环丙烷的还原开环。还原性开环过程中存在抗还原亲电子试剂,例如甲氧基频哪醇硼烷、环氧化物、氧杂环丁烷、多聚甲醛或氯三甲基硅烷,导致通过立即捕获所得两个反应性碳负离子形成 1,3-双官能化 1-芳基烷烃. 特别是,芳基环丙烷的开环 1,3-二硼基化提供了具有高顺式选择性的 1,3-二硼基烷烃。
更新日期:2020-10-22
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