10.1021/acs.joc.5b02088.s002
Peng-Ju Xia
Peng-Ju
Xia
Yan-Hua Sun
Yan-Hua
Sun
Jun-An Xiao
Jun-An
Xiao
Zhao-Fang Zhou
Zhao-Fang
Zhou
Sai-Shuai Wen
Sai-Shuai
Wen
Yu Xiong
Yu
Xiong
Guang-Chuan Ou
Guang-Chuan
Ou
Xiao-Qing Chen
Xiao-Qing
Chen
Hua Yang
Hua
Yang
Regioselectivity-Tunable
Self-1,3-Dipolar [3+3] Cyclizations
of Azomethine Ylides To Assemble Dispirooxindole-piperazines
American Chemical Society
2015
isomer
skeleton
series
Cyclization
amines
regioselectivity
azomethine ylides
cyclization
scaffold
diastereoselectivity
tetrahydroisoquinoline
pyrrolidine
substrate
cyclic
Azomethine Ylides
isatin
glycine methyl ester
2015-11-20 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Regioselectivity_Tunable_Self_1_3_Dipolar_3_3_Cyclizations_of_Azomethine_Ylides_To_Assemble_Dispirooxindole_piperazines/2106709
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).