磺酰
化学
环异构化
立体选择性
砜
硫黄
药物化学
组合化学
立体化学
有机化学
催化作用
烷基
作者
Raju Jannapu Reddy,Jangam Jagadesh Kumar,Arram Haritha Kumari
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-03-29
卷期号:25 (13): 2207-2212
被引量:2
标识
DOI:10.1021/acs.orglett.3c00309
摘要
Cycloannulative sulfonyl migration has received much attention; however, a carbon-to-carbon sulfonyl group shift still needs to be discovered. We hereby report a base-mediated oxa-Michael addition-elimination of (E)-β-iodovinyl sulfones with ortho-alkynylphenols, followed by cycloisomerization and unique stereoselective sulfonyl migration in one-pot, is realized under the influence of Mn(OAc)3·2H2O. A broad range of vinyl sulfone-tethered chromenes were readily accessed in moderate to high yields with good functional group compatibility. Notably, the reaction was robust at the gram scale, and postsynthetic transformations were successfully uncovered. Moreover, plausible mechanistic pathways were rationalized on the basis of existing experimental results.
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