Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China.
J Am Chem Soc. 2011 Aug 17;133(32):12394-7. doi: 10.1021/ja2046217. Epub 2011 Jul 25.
A highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines has been developed. The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions is the key to achieving high yield and enantioselectivity. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure. Furthermore, excellent results are also obtained for the imine substrates with the more readily cleavable N-nosyl protecting group.
已开发出一种高对映选择性的铑催化脂肪族 N-对甲苯磺酰亚胺的芳基化反应。手性双环[3.3.0]辛二烯配体、活性的氢氧化铑配合物以及中性反应条件的组合是实现高产率和对映选择性的关键。该方法的应用通过一锅法中的对映选择性合成手性 2-芳基吡咯烷和哌啶得到了证明。此外，对于更易裂解的 N-硝磺酰保护基的亚胺底物也获得了优异的结果。
