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通过膦介导的醛、α-卤代羰基化合物和末端烯烃的三组分体系立体选择性合成多取代烯烃。

Stereoselective synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, alpha-halo carbonyl compounds, and terminal alkenes.

作者信息

Liu Da-Neng, Tian Shi-Kai

机构信息

Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, China.

出版信息

Chemistry. 2009;15(18):4538-42. doi: 10.1002/chem.200900177.

DOI:10.1002/chem.200900177
PMID:19301331
Abstract

Geometrical control: PPh(3) and methyl acrylate (or acrylamide) are able to mediate the one-pot Wittig reaction of aldehydes with alpha-halo carbonyl compounds for the synthesis of 1,2-disubstituted and trisubstituted alkenes in an excellent stereoselective fashion. Furthermore, the first one-pot, three-component reaction of aldehydes, alpha-halo acetates, and terminal alkenes has been developed in the presence of PPh(3) to produce trisubstituted alkenes with excellent E selectivity (see scheme).

摘要

几何控制

三苯基膦(PPh(3))与丙烯酸甲酯(或丙烯酰胺)能够介导醛与α-卤代羰基化合物的一锅法维蒂希反应,以优异的立体选择性合成1,2-二取代和三取代烯烃。此外,已开发出在三苯基膦(PPh(3))存在下醛、α-卤代乙酸酯和末端烯烃的首个一锅法三组分反应,以优异的E选择性生成三取代烯烃(见方案)。

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