Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2‑Hydroxy-3-oxo-2,3-dihydro‑1H‑pyrrole-2-carboxylates.

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Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2‑Hydroxy-3-oxo-2,3-dihydro‑1H‑pyrrole-2-carboxylates. / Занахов, Тимур Олегович ; Галенко, Екатерина Евгениевна ; Новиков, Михаил Сергеевич ; Хлебников, Александр Феодосиевич.

In: Journal of Organic Chemistry, Vol. 87, No. 22, 18.11.2022, p. 15598-15607.

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

BibTeX

@article{445fdd2287c640c2a43e5cf3c360f123,

title = "Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2‑Hydroxy-3-oxo-2,3-dihydro‑1H‑pyrrole-2-carboxylates.",

abstract = "A diazo strategy for the intramolecular azirine ring expansion was developed. Azirinyl-substituted diazodicarbonyl compounds, prepared from diazoacetylazirines, were converted in excellent yields to 2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates under Rh catalysis in the presence of water. According to DFT calculations, the formation of only pyrrolinone derivatives and the absence of O-H insertion products of Rh carbene into water are due to the low Gibbs free energy of the transition state for the concerted opening of the azirine ring and recyclization to pyrrolone in intermediate Rh complexes.",

author = "Занахов, {Тимур Олегович} and Галенко, {Екатерина Евгениевна} and Новиков, {Михаил Сергеевич} and Хлебников, {Александр Феодосиевич}",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = nov,

day = "18",

doi = "10.1021/acs.joc.2c02177",

language = "English",

volume = "87",

pages = "15598--15607",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "22",

}

RIS

TY - JOUR

T1 - Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2‑Hydroxy-3-oxo-2,3-dihydro‑1H‑pyrrole-2-carboxylates.

AU - Занахов, Тимур Олегович

AU - Галенко, Екатерина Евгениевна

AU - Новиков, Михаил Сергеевич

AU - Хлебников, Александр Феодосиевич

PY - 2022/11/18

Y1 - 2022/11/18

N2 - A diazo strategy for the intramolecular azirine ring expansion was developed. Azirinyl-substituted diazodicarbonyl compounds, prepared from diazoacetylazirines, were converted in excellent yields to 2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates under Rh catalysis in the presence of water. According to DFT calculations, the formation of only pyrrolinone derivatives and the absence of O-H insertion products of Rh carbene into water are due to the low Gibbs free energy of the transition state for the concerted opening of the azirine ring and recyclization to pyrrolone in intermediate Rh complexes.

AB - A diazo strategy for the intramolecular azirine ring expansion was developed. Azirinyl-substituted diazodicarbonyl compounds, prepared from diazoacetylazirines, were converted in excellent yields to 2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates under Rh catalysis in the presence of water. According to DFT calculations, the formation of only pyrrolinone derivatives and the absence of O-H insertion products of Rh carbene into water are due to the low Gibbs free energy of the transition state for the concerted opening of the azirine ring and recyclization to pyrrolone in intermediate Rh complexes.

UR - http://www.scopus.com/inward/record.url?scp=85141598251&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/a062e424-c9ea-36bc-b7a0-81934f129e7f/

U2 - 10.1021/acs.joc.2c02177

DO - 10.1021/acs.joc.2c02177

M3 - Article

VL - 87

SP - 15598

EP - 15607

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 22

ER -

ID: 100120323