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Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones
Author(s) -
Kimura Jo,
Subba Reddy Ummareddy Venkata,
Kohari Yoshihito,
Seki Chigusa,
Mawatari Yasuteru,
Uwai Koji,
Okuyama Yuko,
Kwon Eunsang,
Tokiwa Michio,
Takeshita Mitsuhiro,
Iwasa Tatsuo,
Nakano Hiroto
Publication year - 2016
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.201600414
Subject(s) - chemistry , enantioselective synthesis , aldol reaction , amide , organocatalysis , catalysis , organic chemistry , isatin , combinatorial chemistry
Enantioselective aldol reactions of various isatins with ketones using newly designed amino amide organocatalysts were found to provide chiral 3‐substituted 3‐hydroxy‐2‐oxindoles in good to excellent yields and with excellent stereoselectivities (up to 99 %, up to 98 % ee , syn/anti = 99:1); one catalyst, 3i , proved particularly successful. One of the resulting oxindoles, 3‐hydroxy‐3‐(2‐oxocyclohexyl)‐2‐indolinone may serve as a synthetic intermediate for pharmaceutically important compounds and, in its own right, shows interesting anticonvulsant activities.