Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones

Jo Kimura; Ummareddy Venkata Subba Reddy; Yoshihito Kohari; Chigusa Seki; Yasuteru Mawatari; Koji Uwai; Yuko Okuyama; Eunsang Kwon; Michio Tokiwa; Mitsuhiro Takeshita; Tatsuo Iwasa; Hiroto Nakano

doi:10.1002/ejoc.201600414

Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones

Jo Kimura, Ummareddy Venkata Subba Reddy, Yoshihito Kohari, Chigusa Seki, Yasuteru Mawatari, Koji Uwai, Yuko Okuyama, Eunsang Kwon, Michio Tokiwa, Mitsuhiro Takeshita, Tatsuo Iwasa, Hiroto Nakano

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3748-3756
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	22
DOIs	https://doi.org/10.1002/ejoc.201600414
Publication status	Published - 2016 Aug

Keywords

3-Hydroxy-2-oxindole
Aldol reactions
Amino amide
Enantioselectivity
Isatin
Organocatalysis

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10.1002/ejoc.201600414

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title = "Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones",

abstract = "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.",

keywords = "3-Hydroxy-2-oxindole, Aldol reactions, Amino amide, Enantioselectivity, Isatin, Organocatalysis",

author = "Jo Kimura and {Subba Reddy}, {Ummareddy Venkata} and Yoshihito Kohari and Chigusa Seki and Yasuteru Mawatari and Koji Uwai and Yuko Okuyama and Eunsang Kwon and Michio Tokiwa and Mitsuhiro Takeshita and Tatsuo Iwasa and Hiroto Nakano",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = aug,

doi = "10.1002/ejoc.201600414",

language = "English",

volume = "2016",

pages = "3748--3756",

journal = "European Journal of Organic Chemistry",

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T1 - Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones

AU - Kimura, Jo

AU - Subba Reddy, Ummareddy Venkata

AU - Kohari, Yoshihito

AU - Seki, Chigusa

AU - Mawatari, Yasuteru

AU - Uwai, Koji

AU - Okuyama, Yuko

AU - Kwon, Eunsang

AU - Tokiwa, Michio

AU - Takeshita, Mitsuhiro

AU - Iwasa, Tatsuo

AU - Nakano, Hiroto

PY - 2016/8

Y1 - 2016/8

N2 - 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.

AB - 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.

KW - 3-Hydroxy-2-oxindole

KW - Aldol reactions

KW - Amino amide

KW - Enantioselectivity

KW - Isatin

KW - Organocatalysis

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U2 - 10.1002/ejoc.201600414

DO - 10.1002/ejoc.201600414

M3 - Article

AN - SCOPUS:84978229432

SN - 1434-193X

VL - 2016

SP - 3748

EP - 3756

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 22

ER -

Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones

Abstract

Keywords

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