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手性 α,β-不饱和羰基化合物与二芳基酮的电化学偶联：4,5,5-三取代 γ-丁内酯的不对称合成。

Electroreductive coupling of optically active α,β-unsaturated carbonyl compounds with diaryl ketones: asymmetric synthesis of 4,5,5-trisubstituted γ-butyrolactones.

机构信息

Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University , 4-101, Koyama-cho Minami, Tottori 680-8552, Japan.

出版信息

Org Lett. 2014 Jun 20;16(12):3348-51. doi: 10.1021/ol5013789. Epub 2014 Jun 5.

DOI:10.1021/ol5013789
PMID:24901637
Abstract

The electroreductive coupling of optically active N-E-crotonoyl- and N-cinnamoylimidazolidin-2-ones and oxazolidin-2-ones with diaryl ketones in the presence of chlorotrimethylsilane gave adducts with high diastereoselectivity. The adducts were readily transformed to optically active 4,5,5-trisubstituted γ-butyrolactones by treatment with TBAF.

摘要

在三甲基氯硅烷的存在下，通过光活性的 N-E-丙烯酰基-和 N-肉桂酰基咪唑烷-2-酮与二芳基酮的电还原偶联，得到具有高非对映选择性的加合物。这些加合物通过用 TBAF 处理，很容易转化为光学活性的 4,5,5-三取代的γ-丁内酯。

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