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Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes : A Route to 2-Benzoxepines. / Inyutina, Anna; Kantin, Grigory; Dar'In, Dmitry; Krasavin, Mikhail.

в: Journal of Organic Chemistry, Том 86, № 19, 01.10.2021, стр. 13673–13683.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Inyutina, A, Kantin, G, Dar'In, D & Krasavin, M 2021, 'Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines', Journal of Organic Chemistry, Том. 86, № 19, стр. 13673–13683. https://doi.org/10.1021/acs.joc.1c01710

APA

Inyutina, A., Kantin, G., Dar'In, D., & Krasavin, M. (2021). Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines. Journal of Organic Chemistry, 86(19), 13673–13683. https://doi.org/10.1021/acs.joc.1c01710

Vancouver

Inyutina A, Kantin G, Dar'In D, Krasavin M. Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines. Journal of Organic Chemistry. 2021 Окт. 1;86(19):13673–13683. https://doi.org/10.1021/acs.joc.1c01710

Author

Inyutina, Anna ; Kantin, Grigory ; Dar'In, Dmitry ; Krasavin, Mikhail. / Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes : A Route to 2-Benzoxepines. в: Journal of Organic Chemistry. 2021 ; Том 86, № 19. стр. 13673–13683.

BibTeX

@article{f2815e7f5426408ba6b6750e1b4aa4dd,
title = "Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines",
abstract = "We report on a facile method for the preparation of 2-benzoxepine derivatives as a result of Rh(II)-catalyzed decomposition of diazo arylidene succinimides in the presence of aldehydes. The process is thought to involve the formation of styryl carbonyl ylide which undergoes 1,7-electrocyclization and subsequent 1,5-hydrogen shift. In some cases, the competition of the target reaction and [3+2] dipolar cycloaddition of the intermediate carbonyl ylide to another molecule of diazo substrate was observed. Generally, the desired 2-benzoxepines were isolated in good to high yields and high diastereoselectivity. The developed original approach toward a 2-benzoxepine core via formal [5+2] cycloaddition of styryl carbenoids and aldehydes significantly expands the arsenal of synthetic methods for producing this scaffold. ",
keywords = "CARBONYL YLIDE REACTIONS, DIOSCOREALIDE B, VINYL, DIHYDROFURANS, BENZYLIDENE, METABOLITES, DERIVATIVES",
author = "Anna Inyutina and Grigory Kantin and Dmitry Dar'In and Mikhail Krasavin",
note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",
year = "2021",
month = oct,
day = "1",
doi = "10.1021/acs.joc.1c01710",
language = "English",
volume = "86",
pages = "13673–13683",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "19",

}

RIS

TY - JOUR

T1 - Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes

T2 - A Route to 2-Benzoxepines

AU - Inyutina, Anna

AU - Kantin, Grigory

AU - Dar'In, Dmitry

AU - Krasavin, Mikhail

N1 - Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - We report on a facile method for the preparation of 2-benzoxepine derivatives as a result of Rh(II)-catalyzed decomposition of diazo arylidene succinimides in the presence of aldehydes. The process is thought to involve the formation of styryl carbonyl ylide which undergoes 1,7-electrocyclization and subsequent 1,5-hydrogen shift. In some cases, the competition of the target reaction and [3+2] dipolar cycloaddition of the intermediate carbonyl ylide to another molecule of diazo substrate was observed. Generally, the desired 2-benzoxepines were isolated in good to high yields and high diastereoselectivity. The developed original approach toward a 2-benzoxepine core via formal [5+2] cycloaddition of styryl carbenoids and aldehydes significantly expands the arsenal of synthetic methods for producing this scaffold.

AB - We report on a facile method for the preparation of 2-benzoxepine derivatives as a result of Rh(II)-catalyzed decomposition of diazo arylidene succinimides in the presence of aldehydes. The process is thought to involve the formation of styryl carbonyl ylide which undergoes 1,7-electrocyclization and subsequent 1,5-hydrogen shift. In some cases, the competition of the target reaction and [3+2] dipolar cycloaddition of the intermediate carbonyl ylide to another molecule of diazo substrate was observed. Generally, the desired 2-benzoxepines were isolated in good to high yields and high diastereoselectivity. The developed original approach toward a 2-benzoxepine core via formal [5+2] cycloaddition of styryl carbenoids and aldehydes significantly expands the arsenal of synthetic methods for producing this scaffold.

KW - CARBONYL YLIDE REACTIONS

KW - DIOSCOREALIDE B

KW - VINYL

KW - DIHYDROFURANS

KW - BENZYLIDENE

KW - METABOLITES

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85115954885&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.1c01710

DO - 10.1021/acs.joc.1c01710

M3 - Article

AN - SCOPUS:85115954885

VL - 86

SP - 13673

EP - 13683

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -

ID: 86412666