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Hybrid‐Type Squaramide‐Fused Amino Alcohol Organocatalysts for Enantioselective Nitro‐Aldol Reaction of Nitromethane with Isatins
Author(s) -
Chennapuram Madhu,
Subba Reddy U. V.,
Seki Chigusa,
Okuyama Yuko,
Kwon Eunsang,
Uwai Koji,
Tokiwa Michio,
Takeshita Mitsuhiro,
Nakano Hiroto
Publication year - 2017
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.201700138
Subject(s) - nitromethane , squaramide , aldol reaction , enantioselective synthesis , chemistry , alcohol , nitro , organic chemistry , catalysis , organocatalysis , combinatorial chemistry , alkyl
A series of hybrid‐type squaramide‐fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro‐aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3‐substituted 3‐hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee ). The resulting chiral 3‐hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.