Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes
Ilia A Smetanin
1, 2, 3, 4, 5
,
Anastasiya V Agafonova
1, 2, 3, 4, 5
,
Nikolai V Rostovskii
1, 2, 3, 4, 5
,
Alexander F Khlebnikov
1, 2, 3, 4, 5
,
Dmitry S. Yufit
6
,
Mikhail S. Novikov
1, 2, 3, 4, 5
3
Institute of Chemistry
4
St. Petersburg
5
Russia
|
Publication type: Journal Article
Publication date: 2020-01-01
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Abstract
A two-step method for the preparation of 3,4-epoxypyrroline derivatives (6-oxa-3-azabicyclo[3.1.0]hex-2-enes) from 2-halo-2H-azirine-2-carboxylates, diazo keto esters, and amines has been developed. 6-Halo-1-oxa-4-azahexa-1,3,5-trienes, prepared in the first step from the azirines and diazo compounds under Rh(II) catalysis, were subjected to nucleophile-induced tandem cyclization to afford highly functionalized rac-(1R,4R,5S)-6-oxa-3-azabicyclo[3.1.0]hex-2-enes in good yields. The stereochemical outcome of the tandem cyclization induced by the secondary amines is rationalized in terms of the structural rigidity of the betaine-type precursor due to the hydrogen bonding between the ammonium group and ester group adjacent to the halogen atom. Post-modification of the 3,4-epoxypyrrolines by the Stille cross-coupling, reduction, and UV-irradiation was also demonstrated.
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Total citations:
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Citations from 2024:
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(66%)
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Smetanin I. A. et al. Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes // Organic Chemistry Frontiers. 2020. Vol. 7. No. 3. pp. 525-530.
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Smetanin I. A., Agafonova A. V., Rostovskii N. V., Khlebnikov A. F., Yufit D. S., Novikov M. S. Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes // Organic Chemistry Frontiers. 2020. Vol. 7. No. 3. pp. 525-530.
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TY - JOUR
DO - 10.1039/c9qo01401b
UR - https://xlink.rsc.org/?DOI=C9QO01401B
TI - Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes
T2 - Organic Chemistry Frontiers
AU - Smetanin, Ilia A
AU - Agafonova, Anastasiya V
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Yufit, Dmitry S.
AU - Novikov, Mikhail S.
PY - 2020
DA - 2020/01/01
PB - Royal Society of Chemistry (RSC)
SP - 525-530
IS - 3
VL - 7
SN - 2052-4110
SN - 2052-4129
ER -
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BibTex (up to 50 authors)
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@article{2020_Smetanin,
author = {Ilia A Smetanin and Anastasiya V Agafonova and Nikolai V Rostovskii and Alexander F Khlebnikov and Dmitry S. Yufit and Mikhail S. Novikov},
title = {Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes},
journal = {Organic Chemistry Frontiers},
year = {2020},
volume = {7},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=C9QO01401B},
number = {3},
pages = {525--530},
doi = {10.1039/c9qo01401b}
}
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MLA
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Smetanin, Ilia A., et al. “Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes.” Organic Chemistry Frontiers, vol. 7, no. 3, Jan. 2020, pp. 525-530. https://xlink.rsc.org/?DOI=C9QO01401B.