Asymmetric Organocatalytic Michael Addition-Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles

Estelle Silm; Sandra Kaabel; Ivar Järving; Tõnis Kanger

doi:10.1055/s-0039-1690484

Asymmetric Organocatalytic Michael Addition-Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles

Estelle Silm, 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

4 Citations (Scopus)

Abstract

An asymmetric organocatalytic cascade reaction between cyclopentane-1,2-diones and alkylidene malononitriles affords highly substituted 4 H-pyrans in moderate to high enantiomeric excess. The selective reduction of a bridged double bond leads to the formation of cis-substituted cyclopentanone with three contiguous stereogenic centres.

Original language	English
Pages (from-to)	4198-4204
Number of pages	7
Journal	Synthesis (Germany)
Volume	51
Issue number	22
DOIs	https://doi.org/10.1055/s-0039-1690484
Publication status	Published - 2019
MoE publication type	A1 Journal article-refereed

Keywords

asymmetric catalysis
cascade reaction
diketone
organocatalysis
pyran

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abstract = "An asymmetric organocatalytic cascade reaction between cyclopentane-1,2-diones and alkylidene malononitriles affords highly substituted 4 H-pyrans in moderate to high enantiomeric excess. The selective reduction of a bridged double bond leads to the formation of cis-substituted cyclopentanone with three contiguous stereogenic centres.",

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AU - Järving, Ivar

AU - Kanger, Tõnis

PY - 2019

Y1 - 2019

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KW - cascade reaction

KW - diketone

KW - organocatalysis

KW - pyran

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Asymmetric Organocatalytic Michael Addition-Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles

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Keywords

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