Standard

α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis. / Synofzik, Judith; Dar'In, Dmitry; Novikov, Mikhail S.; Kantin, Grigory; Bakulina, Olga; Krasavin, Mikhail.

в: Journal of Organic Chemistry, Том 84, № 18, 20.09.2019, стр. 12101-12110.

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

Harvard

Synofzik, J, Dar'In, D, Novikov, MS, Kantin, G, Bakulina, O & Krasavin, M 2019, 'α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis', Journal of Organic Chemistry, Том. 84, № 18, стр. 12101-12110. https://doi.org/10.1021/acs.joc.9b02030

APA

Synofzik, J., Dar'In, D., Novikov, M. S., Kantin, G., Bakulina, O., & Krasavin, M. (2019). α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis. Journal of Organic Chemistry, 84(18), 12101-12110. https://doi.org/10.1021/acs.joc.9b02030

Vancouver

Synofzik J, Dar'In D, Novikov MS, Kantin G, Bakulina O, Krasavin M. α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis. Journal of Organic Chemistry. 2019 Сент. 20;84(18):12101-12110. https://doi.org/10.1021/acs.joc.9b02030

Author

Synofzik, Judith ; Dar'In, Dmitry ; Novikov, Mikhail S. ; Kantin, Grigory ; Bakulina, Olga ; Krasavin, Mikhail. / α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis. в: Journal of Organic Chemistry. 2019 ; Том 84, № 18. стр. 12101-12110.

BibTeX

@article{e0cfbc0217994e919511c8d0d8b09259,
title = "α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis",
abstract = "Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.",
keywords = "CASTAGNOLI-CUSHMAN REACTION, PRODUCT SPACE, CYCLOADDITION, ACYLKETENES, IMINES",
author = "Judith Synofzik and Dmitry Dar'In and Novikov, {Mikhail S.} and Grigory Kantin and Olga Bakulina and Mikhail Krasavin",
year = "2019",
month = sep,
day = "20",
doi = "10.1021/acs.joc.9b02030",
language = "English",
volume = "84",
pages = "12101--12110",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "18",

}

RIS

TY - JOUR

T1 - α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

AU - Synofzik, Judith

AU - Dar'In, Dmitry

AU - Novikov, Mikhail S.

AU - Kantin, Grigory

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2019/9/20

Y1 - 2019/9/20

N2 - Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

AB - Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

KW - CASTAGNOLI-CUSHMAN REACTION

KW - PRODUCT SPACE

KW - CYCLOADDITION

KW - ACYLKETENES

KW - IMINES

UR - http://www.scopus.com/inward/record.url?scp=85072508895&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/%CE%B1acyl%CE%B1diazoacetates-transitionmetalfree-%CE%B2lactam-synthesis

U2 - 10.1021/acs.joc.9b02030

DO - 10.1021/acs.joc.9b02030

M3 - Article

C2 - 31433643

AN - SCOPUS:85072508895

VL - 84

SP - 12101

EP - 12110

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -

ID: 49034447