Journal of Organic Chemistry

, том 84 , издание 18 , страницы 12101-12110

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

Тип публикации: Journal Article

Дата публикации: 2019-08-21

American Chemical Society (ACS)

Journal of Organic Chemistry

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SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b02030

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PubMed ID: 31433643

Organic Chemistry

Краткое описание

Thermally promoted reaction of alpha-acyl-alpha-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers alpha-alkoxycarbonyl-substituted beta-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 beta-lactams.

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Synofzik J. et al. α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis // Journal of Organic Chemistry. 2019. Vol. 84. No. 18. pp. 12101-12110.

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Synofzik J., Dar’in D., Novikov M. S., Kantin G., Bakulina O., Krasavin M. α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis // Journal of Organic Chemistry. 2019. Vol. 84. No. 18. pp. 12101-12110.

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TY - JOUR

DO - 10.1021/acs.joc.9b02030

UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b02030

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

T2 - Journal of Organic Chemistry

AU - Synofzik, Judith

AU - Dar’in, Dmitry

AU - Novikov, Mikhail S.

AU - Kantin, Grigory

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2019

DA - 2019/08/21

PB - American Chemical Society (ACS)

SP - 12101-12110

IS - 18

VL - 84

PMID - 31433643

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2019_Synofzik,

author = {Judith Synofzik and Dmitry Dar’in and Mikhail S. Novikov and Grigory Kantin and Olga Bakulina and Mikhail Krasavin},

title = {α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b02030},

number = {18},

pages = {12101--12110},

doi = {10.1021/acs.joc.9b02030}

}

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Synofzik, Judith, et al. “α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis.” Journal of Organic Chemistry, vol. 84, no. 18, Aug. 2019, pp. 12101-12110. https://pubs.acs.org/doi/10.1021/acs.joc.9b02030.