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Organocatalytic amination of pyrazolones with azodicarboxylates: scope and limitations

Organocatalytic amination of pyrazolones with azodicarboxylates: scope and limitations
Organocatalytic amination of pyrazolones with azodicarboxylates: scope and limitations

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.

Amination, Nitrogen heterocycles, Organocatalysis, Synthetic methods
1434-193X
2362-2366
Formánek, Bedřich
7569b4c9-27e3-40bc-beb1-1d6e74cceec1
Šeferna, Vít
9587880a-6083-4da1-9d20-d050bf7bc522
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Patil, Mahendra
00d602a9-34ad-480e-9f6c-6664a9a76334
Veselý, Jan
9d4ecc53-859e-451a-a018-636d416bb3fe
Formánek, Bedřich
7569b4c9-27e3-40bc-beb1-1d6e74cceec1
Šeferna, Vít
9587880a-6083-4da1-9d20-d050bf7bc522
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Patil, Mahendra
00d602a9-34ad-480e-9f6c-6664a9a76334
Veselý, Jan
9d4ecc53-859e-451a-a018-636d416bb3fe

Formánek, Bedřich, Šeferna, Vít, Meazza, Marta, Rios, Ramon, Patil, Mahendra and Veselý, Jan (2021) Organocatalytic amination of pyrazolones with azodicarboxylates: scope and limitations. European Journal of Organic Chemistry, 2021 (17), 2362-2366. (doi:10.1002/ejoc.202100167).

Record type: Article

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.

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2020_Formanek_JV_20Nov - Accepted Manuscript
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More information

Accepted/In Press date: 16 February 2021
e-pub ahead of print date: 10 March 2021
Published date: 7 May 2021
Keywords: Amination, Nitrogen heterocycles, Organocatalysis, Synthetic methods

Identifiers

Local EPrints ID: 448849
URI: http://eprints.soton.ac.uk/id/eprint/448849
DOI: doi:10.1002/ejoc.202100167
ISSN: 1434-193X
PURE UUID: 4e3e2c40-1f36-4001-95e8-f648df92234b
ORCID for Marta Meazza: ORCID iD orcid.org/0000-0003-4382-0626
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 06 May 2021 16:33
Last modified: 18 Mar 2024 05:27

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Contributors

Author: Bedřich Formánek
Author: Vít Šeferna
Author: Marta Meazza ORCID iD
Author: Ramon Rios ORCID iD
Author: Mahendra Patil
Author: Jan Veselý

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