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

Polina S. Teterina, Mariia M. Efremova, Ekaterina V. Sirotkina, Alexander S. Novikov, Olesya V. Khoroshilova, Alexander P. Molchanov

Research output

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.

Original languageEnglish
Article number151063
JournalTetrahedron Letters
DOIs
Publication statusPublished - 1 Jan 2019

Fingerprint

Amino Alcohols
Spironolactone
Cycloaddition
Cycloaddition Reaction
Acetic Acid
Powders
Zinc
nitrones

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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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",
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",
month = "1",
day = "1",
doi = "10.1016/j.tetlet.2019.151063",
language = "English",
journal = "Tetrahedron Letters",
issn = "0040-4039",
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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 - 2019/1/1

Y1 - 2019/1/1

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

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

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 151063

ER -