Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro-furanyl Spirooxindoles

Dmitri Trubitsõn; Sergei Žari; Sandra Kaabel; Marina Kudrjashova; Kadri Kriis; Ivar Järving; Tõnis Pehk; Tõnis Kanger

doi:10.1055/s-0036-1590918

Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro-furanyl Spirooxindoles

Dmitri Trubitsõn, Sergei Žari, Sandra Kaabel, Marina Kudrjashova, Kadri Kriis, Ivar Järving, Tõnis Pehk^*, Tõnis Kanger

^*Corresponding author for this work

Not published at Aalto University

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

8 Citations (Scopus)

Abstract

An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

Original language	English
Pages (from-to)	314-322
Number of pages	9
Journal	Synthesis (Germany)
Volume	50
Issue number	2
DOIs	https://doi.org/10.1055/s-0036-1590918
Publication status	Published - 18 Jan 2018
MoE publication type	A1 Journal article-refereed

Keywords

domino reaction
enantioselectivity
heterocycles
Michael addition
organocatalysis

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title = "Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro-furanyl Spirooxindoles",

abstract = "An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.",

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AU - Trubitsõn, Dmitri

AU - Žari, Sergei

AU - Kaabel, Sandra

AU - Kudrjashova, Marina

AU - Kriis, Kadri

AU - Järving, Ivar

AU - Pehk, Tõnis

AU - Kanger, Tõnis

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PY - 2018/1/18

Y1 - 2018/1/18

N2 - An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

AB - An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

KW - domino reaction

KW - enantioselectivity

KW - heterocycles

KW - Michael addition

KW - organocatalysis

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Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro-furanyl Spirooxindoles

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Keywords

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