用于合成2,3-二氢呋喃的不对称顺序Corey-Chaykovsky环丙烷化/Cloke-Wilson重排反应
Asymmetric Sequential Corey-Chaykovsky Cyclopropanation/Cloke-Wilson Rearrangement for the Synthesis of 2,3-Dihydrofurans.
作者信息
Zhou Yiming, Li Ning, Cai Wei, Huang You
机构信息
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
出版信息
Org Lett. 2021 Nov 19;23(22):8755-8760. doi: 10.1021/acs.orglett.1c03225. Epub 2021 Nov 4.
The first sequential Corey-Chaykovsky cyclopropanation/Cloke-Wilson rearrangement between propargyl sulfonium salts and acrylonitrile derivatives has been developed, affording the tetra-substituted 2,3-dihydrofurans in generally excellent yields (57-98%) with good diastereoselectivities (7:1-18:1). In addition, chiral propargyl sulfonium salt is also suitable for this strategy, giving the optically active 2,3-dihydrofurans with good enantioselectivities. This reaction sequence was designed upon in situ generated 10π-conjugated structures from the dearomatization of indole fragments and subsequent intramolecular 1,6-addition.
首次开发了炔丙基锍盐与丙烯腈衍生物之间的连续Corey-Chaykovsky环丙烷化/Cloke-Wilson重排反应，以通常优异的产率（57-98%）得到四取代的2,3-二氢呋喃，具有良好的非对映选择性（7:1-18:1）。此外，手性炔丙基锍盐也适用于该策略，可得到具有良好对映选择性的光学活性2,3-二氢呋喃。该反应序列是基于吲哚片段脱芳构化原位生成的10π共轭结构以及随后的分子内1,6-加成设计的。
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