Standard

Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines. / Zavyalov, K.V.; Novikov, M.S.; Khlebnikov, A.F.; Yufit, D.S.

в: Tetrahedron, Том 69, № 23, 2013, стр. 4546-4551.

Результаты исследований: Научные публикации в периодических изданиях › статья

Harvard

Zavyalov, KV, Novikov, MS, Khlebnikov, AF & Yufit, DS 2013, 'Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines', Tetrahedron, Том. 69, № 23, стр. 4546-4551. https://doi.org/10.1016/j.tet.2013.04.022

APA

Zavyalov, K. V., Novikov, M. S., Khlebnikov, A. F., & Yufit, D. S. (2013). Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines. Tetrahedron, 69(23), 4546-4551. https://doi.org/10.1016/j.tet.2013.04.022

Vancouver

Zavyalov KV, Novikov MS, Khlebnikov AF, Yufit DS. Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines. Tetrahedron. 2013;69(23):4546-4551. https://doi.org/10.1016/j.tet.2013.04.022

Author

Zavyalov, K.V. ; Novikov, M.S. ; Khlebnikov, A.F. ; Yufit, D.S. / Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines. в: Tetrahedron. 2013 ; Том 69, № 23. стр. 4546-4551.

BibTeX

@article{c157f98beced48f7ad38cab791b1e78a,
title = "Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines",
abstract = "The Rh-2(OAc)(4)-catalyzed reaction of 2H-azirine-2-carbaldehydes with dimethyl diazomalonate proceeds via azirinium ylide formation, isomerization to 2-azabuta-1,3-dienes followed by 1,6-pi-electrocyclization to give 2H-1,3-oxazines. According to DFT-calculations ring opening of azirinium ylides should occur stereoselectively to give 2-azadienes with the C=C bond exclusively in the Z configuration. Changing a formyl group for an acetyl group in the azirine leads to a lowering of stereoselectivity and the formation of azadienes with an E configuration of the C=C bond was observed. The reaction of 2-acy1-2-diazoacetates with 2H-azirine-2-carbaldehydes proceeds similarly, but the 2-acetyl-substituted 2H-1,3-oxazines formed are unstable under chromatographic purification and rearrange easily into pyrrole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.",
author = "K.V. Zavyalov and M.S. Novikov and A.F. Khlebnikov and D.S. Yufit",
year = "2013",
doi = "10.1016/j.tet.2013.04.022",
language = "English",
volume = "69",
pages = "4546--4551",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "23",

}

RIS

TY - JOUR

T1 - Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines

AU - Zavyalov, K.V.

AU - Novikov, M.S.

AU - Khlebnikov, A.F.

AU - Yufit, D.S.

PY - 2013

Y1 - 2013

N2 - The Rh-2(OAc)(4)-catalyzed reaction of 2H-azirine-2-carbaldehydes with dimethyl diazomalonate proceeds via azirinium ylide formation, isomerization to 2-azabuta-1,3-dienes followed by 1,6-pi-electrocyclization to give 2H-1,3-oxazines. According to DFT-calculations ring opening of azirinium ylides should occur stereoselectively to give 2-azadienes with the C=C bond exclusively in the Z configuration. Changing a formyl group for an acetyl group in the azirine leads to a lowering of stereoselectivity and the formation of azadienes with an E configuration of the C=C bond was observed. The reaction of 2-acy1-2-diazoacetates with 2H-azirine-2-carbaldehydes proceeds similarly, but the 2-acetyl-substituted 2H-1,3-oxazines formed are unstable under chromatographic purification and rearrange easily into pyrrole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

AB - The Rh-2(OAc)(4)-catalyzed reaction of 2H-azirine-2-carbaldehydes with dimethyl diazomalonate proceeds via azirinium ylide formation, isomerization to 2-azabuta-1,3-dienes followed by 1,6-pi-electrocyclization to give 2H-1,3-oxazines. According to DFT-calculations ring opening of azirinium ylides should occur stereoselectively to give 2-azadienes with the C=C bond exclusively in the Z configuration. Changing a formyl group for an acetyl group in the azirine leads to a lowering of stereoselectivity and the formation of azadienes with an E configuration of the C=C bond was observed. The reaction of 2-acy1-2-diazoacetates with 2H-azirine-2-carbaldehydes proceeds similarly, but the 2-acetyl-substituted 2H-1,3-oxazines formed are unstable under chromatographic purification and rearrange easily into pyrrole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tet.2013.04.022

DO - 10.1016/j.tet.2013.04.022

M3 - Article

VL - 69

SP - 4546

EP - 4551

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 23

ER -

ID: 7370823