Enantioselective cascade reactions of stable sulfur ylides and nitroolefins through an axial-to-central chirality transfer strategy.
Enantioselective cascade reactions of stable sulfur ylides and nitroolefins through an axial-to-central chirality transfer strategy.
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DOI：
10.1021/jo202324f
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发表时间：
2012-01
期刊：
影响因子：
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通讯作者：
Liang‐Qiu Lu;Z. Ming;J. An;Chao Li;Jia‐Rong Chen;W. Xiao
中科院分区：
文献类型：
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作者：
Liang‐Qiu Lu;Z. Ming;J. An;Chao Li;Jia‐Rong Chen;W. Xiao
使用手性 BINOL 衍生的硫化物作为可靠的立体控制器，通过有效的轴向到中心手性转移，开发了稳定的硫叶立德和硝基烯烃的对映选择性 [4 + 1] 成环/重排级联。它可以以高立体选择性（高达 96:4 e.r. 和 >95:5 d.r.）提供药学和合成上重要的恶唑烷酮。此外，该策略还成功应用于硫叶立德与烯烃系硝基烯烃的不对称[4 + 1]/[3 + 2]环加成级联，并以良好至优异的产率（54-95%产率）获得了相应的对映体富集的稠合杂环（高达87:13 e.r.和> 95:5 d.r.）。
An enantioselective [4 + 1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins has been developed through an efficient axial-to-central chirality transfer with the use of a chiral BINOL-derived sulfide as a reliable stereocontroller. It can provide pharmaceutically and synthetically important oxazolidinones in high stereoselectivities (up to 96:4 e.r. and >95:5 d.r.). Moreover, this strategy was also successfully applied to the asymmetric [4 + 1]/[3 + 2] cycloaddition cascade of sulfur ylides with alkene-tethered nitroolefins, and the corresponding enantioenriched fused heterocycles (up to 87:13 e.r. and >95:5 d.r.) were obtained in good to excellent yields (54-95% yields).