School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG.
Org Biomol Chem. 2010 Mar 7;8(5):1081-90. doi: 10.1039/b919894f. Epub 2010 Jan 5.
A series of enantiopure 2,2'-bipyridines have been synthesised from the corresponding cis-dihydrodiol metabolites of 2-chloroquinolines. Several of the resulting hydroxylated 2,2'-bipyridines were found to be useful chiral ligands for the asymmetric aminolysis of meso-epoxides leading to the formation of enantioenriched amino alcohols (-->84% ee). N-oxide and N,N'-dioxide derivatives of these 2,2'-bipyridines, including separable atropisomers, have been synthesised and used as enantioselective organocatalysts in the asymmetric allylation of aldehydes to give allylic alcohols (-->86% ee).
已经从 2-氯喹啉的相应顺式二氢二醇代谢物合成了一系列对映纯的 2,2'-联吡啶。所得到的几种羟基化的 2,2'-联吡啶被发现是有用的手性配体，用于不对称氨解外消旋环氧，生成对映体富集的氨基醇（-->84%ee）。这些 2,2'-联吡啶的 N-氧化物和 N,N'-二氧化物衍生物，包括可分离的阻转异构体，已被合成并用作不对称烯丙基化醛的手性有机催化剂，以得到烯丙醇（-->86%ee）。
