Chen Liang, Sun Jing, Huang Ying, Zhang Yu, Yan Chao-Guo
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225002, China.
Sci Rep. 2017 Sep 29;7(1):12418. doi: 10.1038/s41598-017-12361-z.
The 1,3-dipolar cycloaddition of active azomethine ylide, which were generated in situ from addition reaction of α-amino acids with dialkyl acetylenedicarboxylates, with 2-arylidene-1,3-indanediones showed versatile regioselectivity and diastereoselectivity. The reaction of sarcosine and glycine afforded one kind of functionalized spiro[indene-2,3'-pyrrolidines]. The other primary α-amino acids such as alanine, phenylalanine and leucine gave another kind of regioisomeric spiro[indene-2,3'-pyrrolidines]. The cyclic α-amino acids resulted in the corresponding spiro[indene-2,2'-pyrrolizines] and [indene-2,6'-pyrrolo[1,2-c]thiazoles].
由α-氨基酸与二烷基乙炔二羧酸酯加成反应原位生成的活性甲亚胺叶立德与2-亚芳基-1,3-茚二酮的1,3-偶极环加成反应表现出多样的区域选择性和非对映选择性。肌氨酸和甘氨酸的反应得到了一种官能化的螺[茚-2,3'-吡咯烷]。其他伯α-氨基酸，如丙氨酸、苯丙氨酸和亮氨酸，则得到了另一种区域异构体螺[茚-2,3'-吡咯烷]。环状α-氨基酸生成了相应的螺[茚-2,2'-吡咯嗪]和[茚-2,6'-吡咯并[1,2-c]噻唑]。
