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A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides. / Teterina, Polina S.; Efremova, Mariia M.; Sirotkina, Ekaterina V.; Novikov, Alexander S.; Khoroshilova, Olesya V.; Molchanov, Alexander P.

In: Tetrahedron Letters, Vol. 60, No. 39, 151063, 2019.

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

Harvard

Teterina, PS, Efremova, MM, Sirotkina, EV, Novikov, AS, Khoroshilova, OV & Molchanov, AP 2019, 'A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides', Tetrahedron Letters, vol. 60, no. 39, 151063. https://doi.org/10.1016/j.tetlet.2019.151063

APA

Teterina, P. S., Efremova, M. M., Sirotkina, E. V., Novikov, A. S., Khoroshilova, O. V., & Molchanov, A. P. (2019). A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides. Tetrahedron Letters, 60(39), [151063]. https://doi.org/10.1016/j.tetlet.2019.151063

Vancouver

Teterina PS, Efremova MM, Sirotkina EV, Novikov AS, Khoroshilova OV, Molchanov AP. A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides. Tetrahedron Letters. 2019;60(39). 151063. https://doi.org/10.1016/j.tetlet.2019.151063

Author

Teterina, Polina S. ; Efremova, Mariia M. ; Sirotkina, Ekaterina V. ; Novikov, Alexander S. ; Khoroshilova, Olesya V. ; Molchanov, Alexander P. / A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides. In: Tetrahedron Letters. 2019 ; Vol. 60, No. 39.

BibTeX

@article{ae04ac11250b4eb59d22a60e60ca375a,
title = "A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides",
abstract = "The 1,3-dipolar cycloaddition of keto- and aldonitrones with N-arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts were subjected to reductive cleavage of the N–O bond using zinc powder in acetic acid to give the corresponding spirolactones and 1,3-amino alcohols.",
keywords = "Cycloaddition, Itaconimides, Nitrones, Reduction, DIASTEREOSELECTIVITY, REGIOSELECTIVITY, PHENYLNITRONES, INHIBITION, NITRILE OXIDES, 1,3-DIPOLAR CYCLOADDITION, BIOLOGICAL EVALUATION, LACTAMS, SPIRO-ISOXAZOLIDINE DERIVATIVES, ALKALOIDS",
author = "Teterina, {Polina S.} and Efremova, {Mariia M.} and Sirotkina, {Ekaterina V.} and Novikov, {Alexander S.} and Khoroshilova, {Olesya V.} and Molchanov, {Alexander P.}",
year = "2019",
doi = "10.1016/j.tetlet.2019.151063",
language = "English",
volume = "60",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "39",

}

RIS

TY - JOUR

T1 - A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides

AU - Teterina, Polina S.

AU - Efremova, Mariia M.

AU - Sirotkina, Ekaterina V.

AU - Novikov, Alexander S.

AU - Khoroshilova, Olesya V.

AU - Molchanov, Alexander P.

PY - 2019

Y1 - 2019

N2 - The 1,3-dipolar cycloaddition of keto- and aldonitrones with N-arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts were subjected to reductive cleavage of the N–O bond using zinc powder in acetic acid to give the corresponding spirolactones and 1,3-amino alcohols.

AB - The 1,3-dipolar cycloaddition of keto- and aldonitrones with N-arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts were subjected to reductive cleavage of the N–O bond using zinc powder in acetic acid to give the corresponding spirolactones and 1,3-amino alcohols.

KW - Cycloaddition

KW - Itaconimides

KW - Nitrones

KW - Reduction

KW - DIASTEREOSELECTIVITY

KW - REGIOSELECTIVITY

KW - PHENYLNITRONES

KW - INHIBITION

KW - NITRILE OXIDES

KW - 1,3-DIPOLAR CYCLOADDITION

KW - BIOLOGICAL EVALUATION

KW - LACTAMS

KW - SPIRO-ISOXAZOLIDINE DERIVATIVES

KW - ALKALOIDS

UR - http://www.scopus.com/inward/record.url?scp=85070855231&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2019.151063

DO - 10.1016/j.tetlet.2019.151063

M3 - Article

AN - SCOPUS:85070855231

VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 39

M1 - 151063

ER -

ID: 45498061