Gold(i)-catalyzed diastereo- and enantioselective [4 + 3] cycloadditions: construction of functionalized furano-benzoxepins
Gold(i)-catalyzed diastereo- and enantioselective [4 + 3] cycloadditions: construction of functionalized furano-benzoxepins
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金 (i) 催化的非对映选择性和对映选择性 [4 3] 环加成：功能化呋喃并苯并氧杂环己烷的构建
DOI：
10.1039/d2qo01070d
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发表时间：
2022
影响因子：
5.4
通讯作者：
Xiaoxun Li
中科院分区：
文献类型：
--
作者：
Xunhua Wang;Ruifeng Lv;Xiaoxun Li
Enantioselective higher-order cycloaddition involving gold-furyl 1,3-dipoles is an attractive but challenging transformation for the construction of chiral polycyclic medium-sized rings from readily available building blocks. Here, gold-catalyzed asymmetric [4 + 3] cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with ortho-quinone methides are reported. A diverse range of functionalized tetrahydro-1-benzoxepins bearing the furan motif have been expediently prepared in good yields with high stereoselectivities (41 examples, up to 95% yield, all >20 : 1 dr, up to 97% ee). The reaction features mild reaction conditions with a broad scope, enabling the late-stage functionalization of important bioactive molecules. Moreover, the enantioenriched benzo[b]oxepin products could be transformed into various substituted furan derivatives.
