Journal of Organic Chemistry

, volume 82 , issue 23 , pages 12827-12833

Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids

Evgeny M Buev ¹

Vladimir S Moshkin ¹

Vyacheslav Ya. Sosnovskikh ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Institute of Natural Sciences and Mathematics, Ural Federal University, 620000 Ekaterinburg, Russian Federation |

Publication type: Journal Article

Publication date: 2017-11-01

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.7b02193

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PubMed ID: 29048900

Organic Chemistry

Abstract

Active methylene compounds react with in situ generated nonstabilized azomethine ylides via the domino Mannich reaction-dipolar cycloaddition to form 3,3-disubstituted pyrrolidines, including oxindole alkaloids. When the starting material possesses a single activated hydrogen, the reaction terminates at the Mannich base stage. The developed methodology was applied to a short and efficient synthesis of (±)-horsfiline and N-protected (±)-coerulescine.

Found

13 citations

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 721 citations

h-index: 30

Ural Federal University

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Buev Evgeny

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Ural Federal University

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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

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Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials

Coordination chemistry of phosphorus

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Aksenov Aleksandr

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Buev E. M., Moshkin V. S., Sosnovskikh V. Y. Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids // Journal of Organic Chemistry. 2017. Vol. 82. No. 23. pp. 12827-12833.

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RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.7b02193

UR - https://doi.org/10.1021/acs.joc.7b02193

TI - Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids

T2 - Journal of Organic Chemistry

AU - Buev, Evgeny M

AU - Moshkin, Vladimir S

AU - Sosnovskikh, Vyacheslav Ya.

PY - 2017

DA - 2017/11/01

PB - American Chemical Society (ACS)

SP - 12827-12833

IS - 23

VL - 82

PMID - 29048900

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2017_Buev,

author = {Evgeny M Buev and Vladimir S Moshkin and Vyacheslav Ya. Sosnovskikh},

title = {Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids},

journal = {Journal of Organic Chemistry},

year = {2017},

volume = {82},

publisher = {American Chemical Society (ACS)},

month = {nov},

url = {https://doi.org/10.1021/acs.joc.7b02193},

number = {23},

pages = {12827--12833},

doi = {10.1021/acs.joc.7b02193}

}

MLA

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MLA Copy

Buev, Evgeny M., et al. “Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids.” Journal of Organic Chemistry, vol. 82, no. 23, Nov. 2017, pp. 12827-12833. https://doi.org/10.1021/acs.joc.7b02193.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)

Labs

Laboratory of Modern Organic Synthesis, INSMa

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