Division of Molecular Synthesis & Drug Discovery, Centre of Biomedical Research, SGPGIMS Campus , Raebareli Road, Lucknow 226014, India.
Org Lett. 2017 Feb 3;19(3):444-447. doi: 10.1021/acs.orglett.6b03501. Epub 2017 Jan 12.
A one-pot, stereoselective construction of 2,3-dihydroxy-2,3-diaryltetrahydrofurans has been achieved via N-heterocyclic carbene (NHC)/base-mediated domino reactions of aldehydes and vinyl selenone. The products containing two contiguous quaternary hydroxyl functionalities among the three stereocenters are obtained advantageously as either acetals or ketals through the formation of five new chemical bonds in a single operation. This report constitutes an altogether different reactivity of vinyl selenone in comparison with the corresponding sulfones and phosphonates under NHC/base-mediated reactions.
通过 N-杂环卡宾（NHC）/碱介导的醛和乙烯基硒酮的多米诺反应，实现了一锅、立体选择性地构建 2,3-二羟基-2,3-二芳基四氢呋喃。通过在单个操作中形成五个新的化学键，有利地获得了在三个立体中心中的两个相邻的季碳羟基官能团的产物，其形式为缩醛或酮。与 NHC/碱介导的反应中相应的砜和膦酸盐相比，本报告构成了乙烯基硒酮的完全不同的反应性。
