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Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p ‐Quinone Methides
Author(s) -
Wang Junwei,
Zhao Lei,
Zhao Lin,
Pan Xiang,
Lv Cheng,
Zhi Ying,
Wang Ai,
Zhao Kun,
Hu Lihong
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000436
Subject(s) - chemistry , annulation , oxindole , quinone methide , quinone , in situ , combinatorial chemistry , manganese , isatin , cascade , stereochemistry , organic chemistry , catalysis , chromatography
Abstract A diastereoselective [4+2] annulation reaction between in situ generated p ‐quinone methides and isatin‐derived enoates has been developed. In the presence of manganese dioxide as an oxidant, a variety of tosylaminophenyl‐substituted p ‐quinone methide intermediates can be readily generated in an in situ fashion. Without pre‐preparation of p ‐QMs, this unprecedented cascade reaction proceeds efficiently under mild conditions, providing a straightforward route to synthesize 4‐phenyl‐substituted tetrahydroquinolines bearing 3,3’‐spirooxindole scaffolds in good yields.