Asymmetric, Organocatalytic, Three-Step Synthesis of γ-Hydroxy-(E)-α,β-Unsaturated Sulfones and Esters
Asymmetric, Organocatalytic, Three-Step Synthesis of γ-Hydroxy-(E)-α,β-Unsaturated Sulfones and Esters
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DOI：
10.1021/ol8020513
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发表时间：
2008-10-16
期刊：
影响因子：
5.2
通讯作者：
Posner, Gary H.
中科院分区：
文献类型：
--
作者：
Petersen, Kimberly S.;Posner, Gary H.
报道了富含对映体的α-硒基醛与EWG稳定的碳负离子反应，然后一锅氧化，原位生成环氧化物，最后原位开环的方法，合成了高效的对映受控的伽马-羟基-α，β-不饱和缩酮和酯。
Efficient and enantiocontrolled synthesis of gamma-hydroxy-alpha,beta-unsaturated sulfones and esters are reported through the reaction of enantioenriched a-selenyl aldehydes with EWG-stabilized carbanions and then a one-pot selenide oxidation, in situ epoxide formation, and final in situ epoxide opening.