The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Org Lett. 2010 Nov 19;12(22):5250-3. doi: 10.1021/ol102292a. Epub 2010 Oct 29.
Organocatalyst-controlled asymmetric anti-Michael reactions of (tert-butyldimethylsilyloxy)acetaldehyde with a range of nitroolefins, followed by an intermolecular aza-Henry reaction with imine, provided iminosugar derivatives with five contiguous stereocenters in very high enantiomeric excess in one pot. The stereochemistry of the aza-Henry reaction was substrate controlled and is explained by a six-membered cyclic transition-state model.
有机催化剂控制的（叔丁基二甲基甲硅烷基氧基）乙醛与一系列硝基烯烃的不对称反迈克尔反应，然后与亚胺进行分子间的氮杂 Henry 反应，一锅法提供了具有五个连续立体中心的氨基糖衍生物，对映过量非常高。氮杂 Henry 反应的立体化学受底物控制，并通过六元环过渡态模型解释。
