volume 84 issue 18 pages 12101-12110

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

Publication typeJournal Article
Publication date2019-08-21
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Abstract
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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MLA Copy
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.