Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

Viktoria A. Ikonnikova; Ekaterina A. Zhigileva; Andrei V. Kuleshov; Vasilissa V. Shirokova; Mikhail S. Baranov; Andrey A. Mikhaylov

doi:10.1016/j.mencom.2021.09.021

Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

Viktoria A. Ikonnikova, Ekaterina A. Zhigileva, Andrei V. Kuleshov, Vasilissa V. Shirokova, Mikhail S. Baranov, Andrey A. Mikhaylov

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

5 Citations (Scopus)

Abstract

Imidazolone-activated donor–acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75–99% yields as mixtures of two diastereomers.

Original language	English
Pages (from-to)	657-658
Number of pages	2
Journal	Mendeleev Communications
Volume	31
Issue number	5
DOIs	https://doi.org/10.1016/j.mencom.2021.09.021
Publication status	Published - 1 Sept 2021
Externally published	Yes

Funding

The authors are grateful to the Russian Science Foundation (grant no. 19-73-00319) for the support of this work.

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1016/j.mencom.2021.09.021

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title = "Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols",

abstract = "Imidazolone-activated donor–acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75–99% yields as mixtures of two diastereomers.",

author = "Ikonnikova, {Viktoria A.} and Zhigileva, {Ekaterina A.} and Kuleshov, {Andrei V.} and Shirokova, {Vasilissa V.} and Baranov, {Mikhail S.} and Mikhaylov, {Andrey A.}",

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doi = "10.1016/j.mencom.2021.09.021",

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T1 - Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

AU - Ikonnikova, Viktoria A.

AU - Zhigileva, Ekaterina A.

AU - Kuleshov, Andrei V.

AU - Shirokova, Vasilissa V.

AU - Baranov, Mikhail S.

AU - Mikhaylov, Andrey A.

PY - 2021/9/1

Y1 - 2021/9/1

N2 - Imidazolone-activated donor–acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75–99% yields as mixtures of two diastereomers.

AB - Imidazolone-activated donor–acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75–99% yields as mixtures of two diastereomers.

UR - http://www.scopus.com/inward/record.url?scp=85119484870&partnerID=8YFLogxK

U2 - 10.1016/j.mencom.2021.09.021

DO - 10.1016/j.mencom.2021.09.021

M3 - Article

AN - SCOPUS:85119484870

SN - 0959-9436

VL - 31

SP - 657

EP - 658

JO - Mendeleev Communications

JF - Mendeleev Communications

IS - 5

ER -

Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

Abstract

Funding

All Science Journal Classification (ASJC) codes

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