Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, People's Republic of China.
Chirality. 2012 Apr;24(4):271-5. doi: 10.1002/chir.21991. Epub 2012 Jan 25.
Several pyrrolidine-camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition-state model was also proposed for this asymmetric transformation, which may involve hydrogen-bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes.
设计并合成了几种吡咯烷-樟脑衍生的有机催化剂。这些有机催化剂被用于醛与硝基烯烃的直接迈克尔加成反应，以高产率（高达 99%）、高非对映选择性（syn:anti 高达 92:8）和良好到优秀的对映选择性（高达 94%ee）得到所需的γ-硝基羰基化合物。还提出了这种不对称转化的可能过渡态模型，该模型可能涉及原位形成的亲核烯胺与硝基烯烃之间的氢键相互作用。
