Enantioselective Synthesis of 3-Heterosubstituted-2-amino-1-ols by Sequential Metal-Free Diene Aziridination/Kinetic Resolution

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

doi:10.1002/chem.201902734

Enantioselective Synthesis of 3-Heterosubstituted-2-amino-1-ols by Sequential Metal-Free Diene Aziridination/Kinetic Resolution

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

Department of Chemistry

Research output: Contribution to journal › Article › Research

1 Citation (Scopus)

Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A general protocol for the enantioselective synthesis of 3-heterosubstituted-2-amino-1-ols was developed based on metal- free intramolecular regio- and stereoselective diene aziridination and regioselective opening. Kinetic resolution of the resulting (1′-NR1R2 and 1′-SR)-4-oxazolidinones was performed using ABCs organocatalysts, expanding the application of this methodology.

Original language	English
Pages (from-to)	12628-12635
Journal	Chemistry - A European Journal
Volume	25
DOIs	https://doi.org/10.1002/chem.201902734
Publication status	Published - 25 Sep 2019

Keywords

ABC catalysts
carbamates kinetic resolution
enantioselectivity
metal-free aziridination
organocatalysis
sphingosine analogues
vinylaziridines synthesis

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10.1002/chem.201902734

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@article{41e0030d6d894fd18beac7dd4fb2ecfb,

title = "Enantioselective Synthesis of 3-Heterosubstituted-2-amino-1-ols by Sequential Metal-Free Diene Aziridination/Kinetic Resolution",

abstract = "{\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A general protocol for the enantioselective synthesis of 3-heterosubstituted-2-amino-1-ols was developed based on metal- free intramolecular regio- and stereoselective diene aziridination and regioselective opening. Kinetic resolution of the resulting (1′-NR1R2 and 1′-SR)-4-oxazolidinones was performed using ABCs organocatalysts, expanding the application of this methodology.",

keywords = "ABC catalysts, carbamates kinetic resolution, enantioselectivity, metal-free aziridination, organocatalysis, sphingosine analogues, vinylaziridines synthesis",

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

year = "2019",

month = sep,

day = "25",

doi = "10.1002/chem.201902734",

language = "English",

volume = "25",

pages = "12628--12635",

}

Enantioselective Synthesis of 3-Heterosubstituted-2-amino-1-ols by Sequential Metal-Free Diene Aziridination/Kinetic Resolution. / Giménez-Nueno, Irene; Guasch, Joan; Funes-Ardoiz, Ignacio; Maseras, Feliu; Matheu, M. Isabel; Castillón, Sergio; Díaz, Yolanda.

In: Chemistry - A European Journal, Vol. 25, 25.09.2019, p. 12628-12635.

Research output: Contribution to journal › Article › Research

TY - JOUR

T1 - Enantioselective Synthesis of 3-Heterosubstituted-2-amino-1-ols by Sequential Metal-Free Diene Aziridination/Kinetic Resolution

AU - Giménez-Nueno, Irene

AU - Guasch, Joan

AU - Funes-Ardoiz, Ignacio

AU - Maseras, Feliu

AU - Matheu, M. Isabel

AU - Castillón, Sergio

AU - Díaz, Yolanda

PY - 2019/9/25

Y1 - 2019/9/25

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AB - © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A general protocol for the enantioselective synthesis of 3-heterosubstituted-2-amino-1-ols was developed based on metal- free intramolecular regio- and stereoselective diene aziridination and regioselective opening. Kinetic resolution of the resulting (1′-NR1R2 and 1′-SR)-4-oxazolidinones was performed using ABCs organocatalysts, expanding the application of this methodology.

KW - ABC catalysts

KW - carbamates kinetic resolution

KW - enantioselectivity

KW - metal-free aziridination

KW - organocatalysis

KW - sphingosine analogues

KW - vinylaziridines synthesis

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DO - 10.1002/chem.201902734

M3 - Article

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