Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

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Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes. / Smetanin, Ilia A.; Agafonova, Anastasiya V.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Yufit, Dmitry S.; Novikov, Mikhail S.

в: Organic Chemistry Frontiers, Том 7, № 3, 07.02.2020, стр. 525-530.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{a3754a206803454aa31b429e7ac7c57d,

title = "Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes",

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.",

keywords = "HUMAN NEUROBLASTOMA-CELLS, EPOLACTAENE DERIVATIVES, RING EXPANSION, ISOXAZOLES, CYCLOADDITION, PYRROLIDINES, SALTS",

author = "Smetanin, {Ilia A.} and Agafonova, {Anastasiya V.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Yufit, {Dmitry S.} and Novikov, {Mikhail S.}",

note = "Funding Information: We gratefully acknowledge the financial support of the Russian Foundation for Basic Research (grant no. 16-03-00596). This research used resources of the Magnetic Resonance Research Centre, Chemical Analysis and Materials Research Centre, Computing Centre, Centre for X-ray Diffraction Studies, and Chemistry Educational Centre of the Research Park of St. Petersburg State University. Publisher Copyright: {\textcopyright} 2020 the Partner Organisations.",

year = "2020",

month = feb,

day = "7",

doi = "10.1039/c9qo01401b",

language = "Английский",

volume = "7",

pages = "525--530",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "3",

}

RIS

TY - JOUR

T1 - Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

AU - Smetanin, Ilia A.

AU - Agafonova, Anastasiya V.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Yufit, Dmitry S.

AU - Novikov, Mikhail S.

N1 - Funding Information: We gratefully acknowledge the financial support of the Russian Foundation for Basic Research (grant no. 16-03-00596). This research used resources of the Magnetic Resonance Research Centre, Chemical Analysis and Materials Research Centre, Computing Centre, Centre for X-ray Diffraction Studies, and Chemistry Educational Centre of the Research Park of St. Petersburg State University. Publisher Copyright: © 2020 the Partner Organisations.

PY - 2020/2/7

Y1 - 2020/2/7

N2 - 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.

AB - 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.

KW - HUMAN NEUROBLASTOMA-CELLS

KW - EPOLACTAENE DERIVATIVES

KW - RING EXPANSION

KW - ISOXAZOLES

KW - CYCLOADDITION

KW - PYRROLIDINES

KW - SALTS

UR - http://www.scopus.com/inward/record.url?scp=85079295063&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/f31f725f-47ba-3f79-b2a2-797a5df52b7d/

U2 - 10.1039/c9qo01401b

DO - 10.1039/c9qo01401b

M3 - статья

VL - 7

SP - 525

EP - 530

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 3

ER -

ID: 51940506