Enantioselective Oxidative Homocoupling of 2-Oxindoles with a Chiral Bisguanidinium Hypoiodite Catalyst DOI
Minami Odagi,

Kazuo Nagasawa,

Yuta Shimizu

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 20, 2024

Abstract The bisoxindole motif is present in a variety of biologically active compounds. Here, we report an enantioselective oxidative homocoupling reaction 2-oxindoles the presence chiral bisguanidinium hypoiodite catalyst, providing access to corresponding optically bisoxindoles excellent yields and with moderate high diastereo- enantioselectivities.

Language: Английский

Dibenzoylperoxide‐Mediated Oxidative α‐Thio/Seleno‐Cyanation of β‐Ketoesters and Oxindoles DOI Creative Commons

Christopher Mairhofer,

Katharina Röser,

Meysam Aryafard

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(46)

Published: Oct. 19, 2023

Abstract We herein report a protocol for the α‐thio‐ and α‐seleno‐cyanation of different cyclic β‐ketoesters oxindoles by using NaSCN or KSeCN as easily accessible inorganic nucleophilic S(e)CN sources under oxidative conditions. Key to success both transformations is use dibenzoylperoxide an oxidant allowing coupling two inherently species operationally simple conditions in high yields with broad functional group tolerance.

Language: Английский

Citations

2
Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide DOI Creative Commons

Christopher Mairhofer,

David Naderer, Mario Waser

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1510 - 1517

Published: July 5, 2024

We herein report the oxidative α-azidation of carbonyl compounds by using NaN 3 in presence dibenzoyl peroxide catalyzed tetrabutylammonium iodide (TBAI). By utilizing these readily available bulk chemicals a variety cyclic β-ketocarbonyl derivatives can be efficiently α-azidated under operationally simple conditions. Control experiments support mechanistic scenario involving situ formation an ammonium hypoiodite species which first facilitates α-iodination pronucleophile, followed phase-transfer-catalyzed nucleophilic substitution azide. Furthermore, we also show that analogous α-nitration NaNO 2 otherwise identical conditions is possible as well.

Language: Английский

Citations

0
Syntheses of diarylmethanes via an oxidative benzylic functionalization of p‐alkyl phenol derivatives under quaternary ammonium hypoiodite catalysis DOI Creative Commons

David Pollheimer,

Christopher Mairhofer,

Mario Waser

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 26, 2024

We herein report two strategies for the quaternary ammonium hypoiodite-mediated oxidative benzylic functionalization of p-alkyl phenol derivatives. By using either dibenzoylperoxide or H

Language: Английский

Citations

0
Enantioselective Oxidative Homocoupling of 2-Oxindoles with a Chiral Bisguanidinium Hypoiodite Catalyst DOI
Minami Odagi,

Kazuo Nagasawa,

Yuta Shimizu

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 20, 2024

Abstract The bisoxindole motif is present in a variety of biologically active compounds. Here, we report an enantioselective oxidative homocoupling reaction 2-oxindoles the presence chiral bisguanidinium hypoiodite catalyst, providing access to corresponding optically bisoxindoles excellent yields and with moderate high diastereo- enantioselectivities.

Language: Английский

Citations

0