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Stereo‐ and Regioselective Construction of Spirooxindoles Having Continuous Spiral Rings via Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Thioaurone Derivatives
Author(s) -
Gui HouZe,
Meng Zhe,
Xiao ZhanShuai,
Yang ZeRen,
Wei Yin,
Shi Min
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001146
Subject(s) - stereocenter , chemistry , regioselectivity , moiety , ring (chemistry) , enantioselective synthesis , yield (engineering) , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
A highly efficient enantioselective [3+2] cyclization of 3‐isothiocyanato oxindoles with thioaurone derivatives was explored for the synthesis of spirooxindoles containing continuous spiral ring structures. Three continuous spiral ring structures and three consecutive chiral centers (including two spiro quaternary stereocenters) were conveniently constructed at a time. In addition, an uncommon sulfur‐containing spirocyclic ring was constructed at the same time. The reaction went smoothly whether the alkenyl moiety of thioaurone derivatives was at 2‐position (up to 99 % yield, up to 99 % ee , up to > 20:1 dr ) or at 3‐position (up to 96 % yield, up to 95 % ee , up to 12:1 dr ).