Umeå University, Department of Chemistry, Linnaeus väg, Umeå SE-90187, Sweden.
Org Biomol Chem. 2011 Jan 21;9(2):337-46. doi: 10.1039/c0ob00336k. Epub 2010 Nov 15.
In this perspective we discuss the recent developments of stereoselective synthesis of substituted pyridines, piperidines, and piperazines from cheap and commercially readily available starting materials. Pyridine N-oxides and pyrazine N-oxides are reacted with alkyl, aryl, alkynyl and vinyl Grignard reagents to give a diverse set of heterocycles in high yields. Optically active substituted piperazines are obtained by an asymmetric reaction from pyrazine N-oxides using sparteine as chiral ligand. In addition, a stereoselective synthesis of dienal-oximes from the reaction between pyridine N-oxides and Grignard reagents is presented, which results in a useful intermediate for the synthesis of a diverse set of compounds.
在这篇观点文章中，我们讨论了最近从廉价且商业上易得的起始原料立体选择性合成取代吡啶、哌啶和哌嗪的进展。吡啶 N-氧化物和哒嗪 N-氧化物与烷基、芳基、炔基和乙烯基格氏试剂反应，以高产率得到多种杂环化合物。使用手性配体辛可宁，通过不对称反应从哒嗪 N-氧化物获得光学活性取代的哌嗪。此外，还提出了从吡啶 N-氧化物和格氏试剂之间的反应制备二烯醛肟的立体选择性合成方法，这是合成多种化合物的有用中间体。
