Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate
Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate
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DOI：
10.1039/d0cc07134j
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发表时间：
2020-12-25
影响因子：
4.9
通讯作者：
Sakakura, Akira
中科院分区：
文献类型：
--
作者：
Mizoguchi, Haruki;Seriu, Masaya;Sakakura, Akira
发展了一种利用硼酸盐络合物的1，2-金属酸盐重排将三溴环丙烷转化为密集官能化的β-硒代环丙基硼酸酯的方法。用苯基硒基氯处理原位生成的环丙烯基硼酸酯络合物引发立体特异性重排以产生官能化的环丙烷。对1，2-金属酸盐重排反应的DFT计算表明，反应是通过硒铱中间体进行的。
A procedure converting tribromocyclopropane to densely functionalized beta-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate.