Enantioselective N-Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis

Arianna Brandolese; Daniele Ragno; Costanza Leonardi; Graziano Di Carmine; Olga Bortolini; Carmela De Risi; Alessandro Massi

doi:10.1002/ejoc.202000151

Enantioselective N-Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis

Arianna Brandolese
, Daniele Ragno
, Costanza Leonardi
, Graziano Di Carmine
, Olga Bortolini
, Carmela De Risi
, Alessandro Massi^*

^*Corresponding author for this work

Chemistry

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

7 Citations (Scopus)

Abstract

The oxidative N-acylation reaction of 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) with enals and N-heterocyclic carbene (NHC) catalysts is described. The reaction proceeds in the presence of quinone oxidant without additional acyl transfer agents and in the asymmetric variant produces pharmaceutically relevant N3-acylated products with good-to-moderate enantioselectivity.

Original language	English
Pages (from-to)	2439-2447
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.202000151
Publication status	Published - 3 May 2020

Bibliographical note

Funding Information:
We gratefully acknowledge the University of Ferrara (fondi FAR) for financial support. Thanks are also given to Paolo Formaglio for NMR experiments and to Tatiana Bernardi for MS analysis.

Publisher Copyright:
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Acylation
Carbenes
Dihydropyrimidines
Organocatalysis
Oxidation

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.202000151

Cite this

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title = "Enantioselective N-Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis",

abstract = "The oxidative N-acylation reaction of 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) with enals and N-heterocyclic carbene (NHC) catalysts is described. The reaction proceeds in the presence of quinone oxidant without additional acyl transfer agents and in the asymmetric variant produces pharmaceutically relevant N3-acylated products with good-to-moderate enantioselectivity.",

keywords = "Acylation, Carbenes, Dihydropyrimidines, Organocatalysis, Oxidation",

author = "Arianna Brandolese and Daniele Ragno and Costanza Leonardi and \{Di Carmine\}, Graziano and Olga Bortolini and \{De Risi\}, Carmela and Alessandro Massi",

note = "Funding Information: We gratefully acknowledge the University of Ferrara (fondi FAR) for financial support. Thanks are also given to Paolo Formaglio for NMR experiments and to Tatiana Bernardi for MS analysis. Publisher Copyright: {\textcopyright} 2020 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2020",

month = may,

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doi = "10.1002/ejoc.202000151",

language = "English",

volume = "2020",

pages = "2439--2447",

journal = "European Journal of Organic Chemistry",

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TY - JOUR

T1 - Enantioselective N-Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis

AU - Brandolese, Arianna

AU - Ragno, Daniele

AU - Leonardi, Costanza

AU - Di Carmine, Graziano

AU - Bortolini, Olga

AU - De Risi, Carmela

AU - Massi, Alessandro

N1 - Funding Information: We gratefully acknowledge the University of Ferrara (fondi FAR) for financial support. Thanks are also given to Paolo Formaglio for NMR experiments and to Tatiana Bernardi for MS analysis. Publisher Copyright: © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/5/3

Y1 - 2020/5/3

N2 - The oxidative N-acylation reaction of 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) with enals and N-heterocyclic carbene (NHC) catalysts is described. The reaction proceeds in the presence of quinone oxidant without additional acyl transfer agents and in the asymmetric variant produces pharmaceutically relevant N3-acylated products with good-to-moderate enantioselectivity.

AB - The oxidative N-acylation reaction of 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) with enals and N-heterocyclic carbene (NHC) catalysts is described. The reaction proceeds in the presence of quinone oxidant without additional acyl transfer agents and in the asymmetric variant produces pharmaceutically relevant N3-acylated products with good-to-moderate enantioselectivity.

KW - Acylation

KW - Carbenes

KW - Dihydropyrimidines

KW - Organocatalysis

KW - Oxidation

UR - https://www.scopus.com/pages/publications/85083826123

U2 - 10.1002/ejoc.202000151

DO - 10.1002/ejoc.202000151

M3 - Article

AN - SCOPUS:85083826123

SN - 1434-193X

VL - 2020

SP - 2439

EP - 2447

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 16

ER -

Enantioselective N-Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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