Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Joan Guasch; Irene Giménez-Nueno; Ignacio Funes-Ardoiz; Miguel Bernús; M. Isabel Matheu; Feliu Maseras; Sergio Castillón; Yolanda Díaz

doi:10.1002/chem.201705670

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Joan Guasch, Irene Giménez-Nueno, Ignacio Funes-Ardoiz, Miguel Bernús, M. Isabel Matheu, Feliu Maseras, Sergio Castillón, Yolanda Díaz

Department of Chemistry

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

13 Citations (Scopus)

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

Original language	English
Pages (from-to)	4635-4642
Journal	Chemistry - A European Journal
Volume	24
Issue number	18
DOIs	https://doi.org/10.1002/chem.201705670
Publication status	Published - 26 Mar 2018

Keywords

enantioselectivity
kinetic resolution
organocatalysis
oxyamination
synthesis design

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10.1002/chem.201705670

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Guasch, J., Giménez-Nueno, I., Funes-Ardoiz, I., Bernús, M., Matheu, M. I., Maseras, F., Castillón, S., & Díaz, Y. (2018). Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis. Chemistry - A European Journal, 24(18), 4635-4642. https://doi.org/10.1002/chem.201705670

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title = "Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis",

abstract = "{\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.",

keywords = "enantioselectivity, kinetic resolution, organocatalysis, oxyamination, synthesis design",

author = "Joan Guasch and Irene Gim{\'e}nez-Nueno and Ignacio Funes-Ardoiz and Miguel Bern{\'u}s and Matheu, {M. Isabel} and Feliu Maseras and Sergio Castill{\'o}n and Yolanda D{\'i}az",

year = "2018",

month = mar,

day = "26",

doi = "10.1002/chem.201705670",

language = "English",

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}

Guasch, J, Giménez-Nueno, I, Funes-Ardoiz, I, Bernús, M, Matheu, MI, Maseras, F, Castillón, S & Díaz, Y 2018, 'Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis', Chemistry - A European Journal, vol. 24, no. 18, pp. 4635-4642. https://doi.org/10.1002/chem.201705670

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis. / Guasch, Joan; Giménez-Nueno, Irene; Funes-Ardoiz, Ignacio et al.
In: Chemistry - A European Journal, Vol. 24, No. 18, 26.03.2018, p. 4635-4642.

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

TY - JOUR

T1 - Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

AU - Guasch, Joan

AU - Giménez-Nueno, Irene

AU - Funes-Ardoiz, Ignacio

AU - Bernús, Miguel

AU - Matheu, M. Isabel

AU - Maseras, Feliu

AU - Castillón, Sergio

AU - Díaz, Yolanda

PY - 2018/3/26

Y1 - 2018/3/26

N2 - © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

AB - © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

KW - enantioselectivity

KW - kinetic resolution

KW - organocatalysis

KW - oxyamination

KW - synthesis design

U2 - 10.1002/chem.201705670

DO - 10.1002/chem.201705670

M3 - Article

SN - 0947-6539

VL - 24

SP - 4635

EP - 4642

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 18

ER -

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Abstract

Keywords

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