Tetrahedron Asymmetry

, volume 25 , issue 2 , pages 141-147

Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers

Zsolt Rapi ¹

Balázs Démuth ¹

György Keglevich ¹

Alajos Grün ^{2, 3}

Laszlo Drahos ^{4, 5, 6}

Péter L Sóti ¹

Péter Bakó ¹

Hide authors affiliations Show authors affiliations: 6 affiliations

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, 1521, Budapest, Hungary |

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, 1521 Budapest, Hungary |

Organic Chemical Technology Research Group of the Hungarian Academy of Sciences, Budapest, Hungary |

⁴

Chemical Research Institute for Chemistry

⁵

HUNGARIAN ACADEMY OF SCIENCES

⁶

H-1525 Budapest Hungary |

Publication type: Journal Article

Publication date: 2014-01-24

Elsevier

Tetrahedron Asymmetry

SJR: —

CiteScore: —

Impact factor: —

ISSN: 09574166, 1362511X

DOI: 10.1016/j.tetasy.2013.12.007

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Catalysis

Organic Chemistry

Inorganic Chemistry

Physical and Theoretical Chemistry

Abstract

The asymmetric Michael addition of diethyl malonate and α-substituted diethyl malonates to aromatic nitroalkenes was carried out under mild reaction conditions in a solid–liquid phase transfer reaction in the presence of α- d -glucopyranoside- and α- d -mannopyranoside-based crown ethers as the catalysts. The use of d -glucose-based lariat ether 1 gave the best results. The substituents of the β-nitrostyrene and the diethyl malonate had a significant impact on the chemical yields and enantioselectivity. The addition of diethyl-2-acetamidomalonate to aromatic nitroalkenes afforded the corresponding Michael adducts in moderate to high enantiomeric excess (ee up to 99%). The reaction of diethyl-2-methylmalonate with 2-nitro-β-nitrostyrene gave the adduct with 93% enantiomeric excess in the presence of crown catalyst 1 .

Found

1 citation

Makarenko Sergey

🥼 🤝

DSc in Chemistry, associate professor

85 publications, 357 citations

h-index: 9

Herzen State Pedagogical University of Russia

Research interests

Organic synthesis

Spectroscopy

1 citation

Pelipko Vasilii

PhD in Chemistry

34 publications, 148 citations

h-index: 7

Herzen State Pedagogical University of Russia

Research interests

Nitroalkenes

Spectroscopy

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Rapi Z. et al. Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers // Tetrahedron Asymmetry. 2014. Vol. 25. No. 2. pp. 141-147.

GOST all authors (up to 50) Copy

Rapi Z., Démuth B., Keglevich G., Grün A., Drahos L., Sóti P. L., Bakó P. Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers // Tetrahedron Asymmetry. 2014. Vol. 25. No. 2. pp. 141-147.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tetasy.2013.12.007

UR - https://doi.org/10.1016/j.tetasy.2013.12.007

TI - Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers

T2 - Tetrahedron Asymmetry

AU - Rapi, Zsolt

AU - Démuth, Balázs

AU - Keglevich, György

AU - Grün, Alajos

AU - Drahos, Laszlo

AU - Sóti, Péter L

AU - Bakó, Péter

PY - 2014

DA - 2014/01/24

PB - Elsevier

SP - 141-147

IS - 2

VL - 25

SN - 0957-4166

SN - 1362-511X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2014_Rapi,

author = {Zsolt Rapi and Balázs Démuth and György Keglevich and Alajos Grün and Laszlo Drahos and Péter L Sóti and Péter Bakó},

title = {Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers},

journal = {Tetrahedron Asymmetry},

year = {2014},

volume = {25},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/j.tetasy.2013.12.007},

number = {2},

pages = {141--147},

doi = {10.1016/j.tetasy.2013.12.007}

}

MLA

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MLA Copy

Rapi, Zsolt, et al. “Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers.” Tetrahedron Asymmetry, vol. 25, no. 2, Jan. 2014, pp. 141-147. https://doi.org/10.1016/j.tetasy.2013.12.007.

Publisher

Elsevier

Journal

Tetrahedron Asymmetry

SJR

—

CiteScore

—

Impact factor

—

ISSN

09574166 (Print)

1362511X (Electronic)