Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations

Bedřich Formánek; Vít Šeferna; Marta Meazza; Ramon Rios; Mahendra Patil; Jan Veselý

doi:10.1002/ejoc.202100167

Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations

Bedřich Formánek
, Vít Šeferna
, Marta Meazza
, Ramon Rios
, Mahendra Patil
, Jan Veselý

Chemistry

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

13 Scopus citations

Abstract

The organocatalytic amination of pyrazol-5-ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74–96 %) and enantioselectivities (up to ee 97 %). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed stereochemical outcome and trends in the effectivity of the reaction.

Original language	British English
Pages (from-to)	2362-2366
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.202100167
State	Published - 7 May 2021

Keywords

Amination
Nitrogen heterocycles
Organocatalysis
Synthetic methods

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10.1002/ejoc.202100167

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title = "Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations",

abstract = "The organocatalytic amination of pyrazol-5-ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74–96 \%) and enantioselectivities (up to ee 97 \%). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed stereochemical outcome and trends in the effectivity of the reaction.",

keywords = "Amination, Nitrogen heterocycles, Organocatalysis, Synthetic methods",

author = "Bed{\v r}ich Form{\'a}nek and V{\'i}t {\v S}eferna and Marta Meazza and Ramon Rios and Mahendra Patil and Jan Vesel{\'y}",

note = "Funding Information: Jan Vesel{\'y} gratefully acknowledges the Czech Science Foundation (No 20‐29336S) for the financial support. Bed{\v r}ich Form{\'a}nek thanks the Charles University Grant Agency (No 393615) for the financial support. We also thank Dr. Simona Petr{\v z}elov{\'a} for the NMR service provided and Dr. Martin {\v S}t{\'i}cha for his MS analysis. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

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doi = "10.1002/ejoc.202100167",

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T1 - Organocatalytic Amination of Pyrazolones with Azodicarboxylates

T2 - Scope and Limitations

AU - Formánek, Bedřich

AU - Šeferna, Vít

AU - Meazza, Marta

AU - Rios, Ramon

AU - Patil, Mahendra

AU - Veselý, Jan

N1 - Funding Information: Jan Veselý gratefully acknowledges the Czech Science Foundation (No 20‐29336S) for the financial support. Bedřich Formánek thanks the Charles University Grant Agency (No 393615) for the financial support. We also thank Dr. Simona Petrželová for the NMR service provided and Dr. Martin Štícha for his MS analysis. Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/5/7

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N2 - The organocatalytic amination of pyrazol-5-ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74–96 %) and enantioselectivities (up to ee 97 %). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed stereochemical outcome and trends in the effectivity of the reaction.

AB - The organocatalytic amination of pyrazol-5-ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74–96 %) and enantioselectivities (up to ee 97 %). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed stereochemical outcome and trends in the effectivity of the reaction.

KW - Amination

KW - Nitrogen heterocycles

KW - Organocatalysis

KW - Synthetic methods

UR - https://www.scopus.com/pages/publications/85102387556

U2 - 10.1002/ejoc.202100167

DO - 10.1002/ejoc.202100167

M3 - Article

AN - SCOPUS:85102387556

SN - 1434-193X

VL - 2021

SP - 2362

EP - 2366

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations

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Keywords

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