Asymmetric organocatalytic aza-michael reactions of isatin derivatives

Sergei Žari; Andrus Metsala; Marina Kudrjashova; Sandra Kaabel; Ivar Järving; Tõnis Kanger

doi:10.1055/s-0034-1379956

Asymmetric organocatalytic aza-michael reactions of isatin derivatives

Sergei Žari, Andrus Metsala, Marina Kudrjashova, Sandra Kaabel, Ivar Järving, Tõnis Kanger^*

^*Corresponding author for this work

Not published at Aalto University

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

14 Citations (Scopus)

Abstract

Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).

Original language	English
Pages (from-to)	875-886
Number of pages	12
Journal	Synthesis (Germany)
Volume	47
Issue number	6
DOIs	https://doi.org/10.1055/s-0034-1379956
Publication status	Published - Mar 2015
MoE publication type	A1 Journal article-refereed

Keywords

asymmetric catalysis
chemoselectivity
enantioselectivity
imines
Michael addition

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abstract = "Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).",

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AU - Žari, Sergei

AU - Metsala, Andrus

AU - Kudrjashova, Marina

AU - Kaabel, Sandra

AU - Järving, Ivar

AU - Kanger, Tõnis

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

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Y1 - 2015/3

N2 - Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).

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KW - asymmetric catalysis

KW - chemoselectivity

KW - enantioselectivity

KW - imines

KW - Michael addition

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ER -

Asymmetric organocatalytic aza-michael reactions of isatin derivatives

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Keywords

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