Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters

Standard

Rh₂(OAc)₄-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters. / Zavyalov, K. V.; Novikov, M. S.; Khlebnikov, A. F.; Rostovskii, N. V.; Starova, G. L.

In: Russian Journal of Organic Chemistry, Vol. 53, No. 8, 2017, p. 1214-1221.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{5511a7f880434ce2b20906e146c38bcb,

title = "Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters",

abstract = "Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters proceeds through an intermediate generation of azirinium ylide suffering a nonstereoselective ring opening to form (3Z)- and (3E)-2-azahexa-1,3,5-trienes. The former depending on configuration of the C5=C6 bond may undergo cyclization either in derivative of 2,3-dihydropyridine, or in pyrrolium ylide that isomerizes into a derivative of 1H-pyrrole. According to DFT calculation, the preferred formation of pyrroles at increasing volume of Z-substituent at the atom C6 and of substituents at the atom C1 of 2-azahexatriene occurs due to the destabilization of more sterically loaded transition states of 1,6-cyclization.",

author = "Zavyalov, {K. V.} and Novikov, {M. S.} and Khlebnikov, {A. F.} and Rostovskii, {N. V.} and Starova, {G. L.}",

year = "2017",

doi = "10.1134/S1070428017080097",

language = "English",

volume = "53",

pages = "1214--1221",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "8",

}

RIS

TY - JOUR

T1 - Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters

AU - Zavyalov, K. V.

AU - Novikov, M. S.

AU - Khlebnikov, A. F.

AU - Rostovskii, N. V.

AU - Starova, G. L.

PY - 2017

Y1 - 2017

N2 - Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters proceeds through an intermediate generation of azirinium ylide suffering a nonstereoselective ring opening to form (3Z)- and (3E)-2-azahexa-1,3,5-trienes. The former depending on configuration of the C5=C6 bond may undergo cyclization either in derivative of 2,3-dihydropyridine, or in pyrrolium ylide that isomerizes into a derivative of 1H-pyrrole. According to DFT calculation, the preferred formation of pyrroles at increasing volume of Z-substituent at the atom C6 and of substituents at the atom C1 of 2-azahexatriene occurs due to the destabilization of more sterically loaded transition states of 1,6-cyclization.

AB - Rh2(OAc)4-catalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2H-azirines with diazo esters proceeds through an intermediate generation of azirinium ylide suffering a nonstereoselective ring opening to form (3Z)- and (3E)-2-azahexa-1,3,5-trienes. The former depending on configuration of the C5=C6 bond may undergo cyclization either in derivative of 2,3-dihydropyridine, or in pyrrolium ylide that isomerizes into a derivative of 1H-pyrrole. According to DFT calculation, the preferred formation of pyrroles at increasing volume of Z-substituent at the atom C6 and of substituents at the atom C1 of 2-azahexatriene occurs due to the destabilization of more sterically loaded transition states of 1,6-cyclization.

UR - http://www.scopus.com/inward/record.url?scp=85029928992&partnerID=8YFLogxK

U2 - 10.1134/S1070428017080097

DO - 10.1134/S1070428017080097

M3 - Article

AN - SCOPUS:85029928992

VL - 53

SP - 1214

EP - 1221

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 8

ER -

ID: 13392662