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不对称催化中的类螺旋手性助剂

Helicene-like chiral auxiliaries in asymmetric catalysis.

作者信息

Aillard P, Voituriez A, Marinetti A

机构信息

Institut de Chimie des Substances Naturelles, CNRS UPR 2301 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France.

出版信息

Dalton Trans. 2014 Nov 7;43(41):15263-78. doi: 10.1039/c4dt01935k.

Abstract

This literature overview demonstrates that helically chiral ligands and organocatalysts have been largely neglected so far. However, a few recent studies on helical pyridine, the corresponding ammonium salts and N-oxides have highlighted the significant potential of these compounds as organocatalysts for Michael type additions, aldehyde propargylations, epoxide openings, and others. In addition, helicenes displaying a fused phosphole ring at the end of their polyaromatic structures, have been used as ligands in enantioselective gold promoted cycloisomerization reactions, giving both excellent catalytic activity and high enantiomeric excesses. These recent results are expected to stimulate further research on the catalytic applications of helically chiral auxiliaries in the next few years.

摘要

这篇文献综述表明,迄今为止,螺旋手性配体和有机催化剂在很大程度上被忽视了。然而,最近一些关于螺旋吡啶、相应的铵盐和氮氧化物的研究突出了这些化合物作为迈克尔型加成、醛炔丙基化、环氧化物开环等反应的有机催化剂的巨大潜力。此外,在其多芳族结构末端带有稠合磷环的螺旋烯,已被用作对映选择性金促进的环异构化反应中的配体,具有出色的催化活性和高对映体过量。预计这些最新结果将在未来几年激发对螺旋手性助剂催化应用的进一步研究。

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