Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Peter Vertesaljai; Primali V. Navaratne; Alexander J. Grenning

doi:10.1002/anie.201508100

Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Peter Vertesaljai, Primali V. Navaratne, Alexander J. Grenning

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

14 Scopus citations

Abstract

Knoevenagel adducts derived from readily available acetoxyacetone and malonic acid derivatives served as trimethylenemethane surrogates for formal 1,3-difunctionalization through a sequence of selective γ-deprotonation/α-alkylation and palladium(0)-catalyzed allylic alkylation. Herein, we report the discovery and development of a three-component 1,3-difunctionalization of Knoevenagel adducts as well as a unique palladium(0)-catalyzed branch-selective allylic alkylation.

Original language	English (US)
Pages (from-to)	317-320
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	1
DOIs	https://doi.org/10.1002/anie.201508100
State	Published - Jan 4 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

1,3-difunctionalization
allylation
Knoevenagel condensation
palladium catalysis
trimethylenemethane

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10.1002/anie.201508100

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abstract = "Knoevenagel adducts derived from readily available acetoxyacetone and malonic acid derivatives served as trimethylenemethane surrogates for formal 1,3-difunctionalization through a sequence of selective γ-deprotonation/α-alkylation and palladium(0)-catalyzed allylic alkylation. Herein, we report the discovery and development of a three-component 1,3-difunctionalization of Knoevenagel adducts as well as a unique palladium(0)-catalyzed branch-selective allylic alkylation.",

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AU - Vertesaljai, Peter

AU - Navaratne, Primali V.

AU - Grenning, Alexander J.

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Y1 - 2016/1/4

N2 - Knoevenagel adducts derived from readily available acetoxyacetone and malonic acid derivatives served as trimethylenemethane surrogates for formal 1,3-difunctionalization through a sequence of selective γ-deprotonation/α-alkylation and palladium(0)-catalyzed allylic alkylation. Herein, we report the discovery and development of a three-component 1,3-difunctionalization of Knoevenagel adducts as well as a unique palladium(0)-catalyzed branch-selective allylic alkylation.

AB - Knoevenagel adducts derived from readily available acetoxyacetone and malonic acid derivatives served as trimethylenemethane surrogates for formal 1,3-difunctionalization through a sequence of selective γ-deprotonation/α-alkylation and palladium(0)-catalyzed allylic alkylation. Herein, we report the discovery and development of a three-component 1,3-difunctionalization of Knoevenagel adducts as well as a unique palladium(0)-catalyzed branch-selective allylic alkylation.

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KW - Knoevenagel condensation

KW - palladium catalysis

KW - trimethylenemethane

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Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Abstract

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