1399086-29-3Relevant academic research and scientific papers
An organocatalytic cascade approach toward polysubstituted quinolines and chiral 1,4-dihydroquinolines-unanticipated effect of N-protecting groups
Zhang, Xinshuai,Song, Xixi,Li, Hao,Zhang, Shilei,Chen, Xiaobei,Yu, Xinhong,Wang, Wei
, p. 7282 - 7286 (2012/09/08)
A matter of protection: The outcome of a divergent organocatalytic aza-Michael/aldol cascade process toward quinolines and 1,4-dihydroquinolines depends on the choice of the N-protecting group (see scheme; TEA=triethylamine, TMS=trimethylsilyl). Use of an electron-donating sulfonyl group results in an unanticipated aza-Michael/aldol/aromatization cascade to give polysubstituted quinolines (right). In contrast, chiral 1,4-dihydroquinolines are obtained with an electron-withdrawing sulfonyl group (left). Copyright
