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Zinc‐Catalyzed Enantioselective Dearomative [3+2] Cycloaddition Reaction of 3‐Nitrobenzothiophenes and 3‐Nitrothieno[2,3‐ b ]yridine with 3‐Isothiocyanato Oxindoles
Author(s) -
Yue DengFeng,
Zhao JianQiang,
Chen YongZheng,
Zhang XiaoMei,
Xu XiaoYing,
Yuan WeiCheng
Publication year - 2018
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.201701557
Subject(s) - enantioselective synthesis , stereocenter , cycloaddition , chemistry , catalysis , oxazoline , zinc , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry
A highly diastereo‐ and enantioselective dearomative [3+2] cycloaddition reaction of 3‐nitrobenzothiophenes and 3‐nitrothieno[2,3‐ b ]with 3‐isothiocyanato oxindoles is developed. The reaction is catalyzed by the chiral Zn(OTf) 2 /bis(oxazoline, and is the second example of a catalytic asymmetric dearomative cycloaddition reaction of 3‐nitrobenzothiophene derivatives. A range of complex heterocyclic compounds containing three contiguous stereocenters, one of which is spirocyclic center, can be obtained in quantitative yields with excellent stereoselectivities.