Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
J Org Chem. 2011 May 20;76(10):4210-2. doi: 10.1021/jo200601y. Epub 2011 Apr 20.
Azomethine ylide formed from glycine methyl ester and cinnamaldehyde adds to N-phenylmaleimide to form pyrrolidine derivative, further treatment of which with cinnamaldehyde and N-phenylmaleimide affords the second [2 + 3] cycloaddition adduct, a pyrrolizine derivative with two styrenyl groups at the 3,5-positions. Addition of ICl to the pyrrolizine derivative results in the 6-exo-trig cyclization of the styrenyl groups to form a cycl[3.2.2]azine derivative. The reactions are highly stereoselective affording 11 chiral carbons in three steps. The structure of the cycl[3.2.2]azine derivative was determined by single-crystal X-ray analysis.
由甘氨酸甲酯和肉桂醛形成的亚甲胺叶立德与 N-苯基马来酰亚胺加成，形成吡咯烷衍生物，进一步用肉桂醛和 N-苯基马来酰亚胺处理该吡咯烷衍生物，得到第二个[2 + 3]环加成加合物，即具有两个乙烯基在 3,5-位的吡咯嗪衍生物。将 ICl 添加到吡咯嗪衍生物中，导致乙烯基在环上的 6-endo-trig 环化，形成环[3.2.2]嗪衍生物。这些反应具有高度的立体选择性，三步即可得到三个手性碳原子。环[3.2.2]嗪衍生物的结构通过单晶 X 射线分析确定。
