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Rh(II)‐Catalyzed Chemoselective Synthesis of 3‐Substituted Oxindoles by C(sp 2 )−H and C(sp 2 )−N Functionalization of β‐Enaminoesters
Author(s) -
Yun Sang Hyeon,
Xia Likai,
Kim Sung Hong,
Lee Yong Rok
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600226
Subject(s) - chemoselectivity , chemistry , surface modification , catalysis , rhodium , nitrogen atom , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry)
A novel chemoselective synthesis of 3‐substituted oxindoles and 3‐substituted 3‐aminooxindoles starting from various 3‐diazoindolin‐2‐ones and β‐enaminoesters was developed through rhodium(II)‐catalyzed C(sp 2 )−H and C(sp 2 )−N functionalization. This protocol provides a rapid synthetic route to a diverse range of 3‐substituted oxindoles and 3‐substituted 3‐aminooxindoles with good yields. The chemoselectivity for the formation of the 3‐substituted oxindoles and 3‐substituted 3‐aminooxindoles was controlled by the substituents on the nitrogen atom of the β‐enaminoesters.