化学
区域选择性
哌嗪
吡咯烷
伊萨丁
立体化学
肌氨酸
戒指(化学)
曼尼希反应
四氢异喹啉
组合化学
甘氨酸
有机化学
氨基酸
生物化学
催化作用
作者
Peng-Ju Xia,Yanhua Sun,Hua Yang,Zhao-Fang Zhou,Sai-Shuai Wen,Yu Xiong,Guang-Chuan Ou,Xiang Chen,Hua Gui Yang
标识
DOI:10.1021/acs.joc.5b02088
摘要
A series of novel 2,3- or 2,5-dispirooxindole-piperazine ring systems were efficiently constructed through the acid-promoted self-1,3-dipolar [3+3] cyclizations of azomethine ylides derived from isatin with various primary or cyclic secondary amines. Interestingly, the regioselectivity of this self-[3+3] cyclization could be effectively tuned by varying the structural features of substrates. The unprecedented 2,5-dispirooxindole-piperazine skeleton was achieved in good diastereoselectivity by employing 1,2,3,4-tetrahydroisoquinoline, while using pyrrolidine or glycine methyl ester furnished the 2,3-dispirooxindole-piperazine scaffold in excellent diastereoselectivity (only a single isomer formed).
科研通智能强力驱动
Strongly Powered by AbleSci AI