One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
复制标题
通过分子内乙烯酮捕获对均炔醇进行一锅 γ-内酯化
DOI：
10.1021/acs.orglett.1c00840
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Ohtawa Masaki
中科院分区：
文献类型：
--
作者：
Yamane Daichi;Tanaka Haruna;Hirata Akihiro;Tamura Yumiko;Takahashi Daichi;Takahashi Yusuke;Nagamitsu Tohru;Ohtawa Masaki
研究了高炔丙醇经炔去质子化/硼化/氧化一锅法γ-内酯化反应。生成的炔基硼酸酯的氧化得到相应的烯酮中间体，其被相邻的羟基捕获以提供γ-内酯。我们优化了反应条件，并考察了这种高效一锅法内酯化反应的底物范围和合成应用。
A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.