Diazo Tetramic Acids Provide Access to Natural-Like Spirocyclic Δ α,β - Butenolides through Rh(II)-Catalyzed O−H Insertion/Base-Promoted Cyclization

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Diazo Tetramic Acids Provide Access to Natural-Like Spirocyclic Δ α,β - Butenolides through Rh(II)-Catalyzed O−H Insertion/Base-Promoted Cyclization. / Дарьин, Дмитрий Викторович ; Кантин, Григорий Павлович; Глушакова, Дарья Валерьевна; Шаройко, Владимир Владимирович ; Красавин, Михаил Юрьевич.

в: Journal of Organic Chemistry, 05.01.2023.

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

BibTeX

@article{962b9180a10b44ea806bbae3cc670fd8,

title = "Diazo Tetramic Acids Provide Access to Natural-Like Spirocyclic Δ α,β - Butenolides through Rh(II)-Catalyzed O−H Insertion/Base-Promoted Cyclization",

abstract = " 3-Diazotetramic acids were found to be validsubstrates for the recently discovered approach toward natural-like Δ α,β -spirobutenolides via Rh(II)-catalyzed O−H insertion intopropiolic acids followed by base-promoted intramolecular Michaeladdition. The target Δ α,β -spirobutenolides were obtained ingenerally high yields and, in the case of chiral 5-monosubstituted3-diazotetramic acids, high diastereoselectivity. The synthesis ofΔ α,β -spirobutenolides that we report here was virtually insensitiveto the structure of the propiolic acids though it was somewhat sensitive to the structure of the 3-diazotetramic acids, therebydemonstrating quite a large scope. Thus, a new class of α-diazocarbonyl compounds suitable for the realization of the approachoutlined above was identified.",

author = "Дарьин, {Дмитрий Викторович} and Кантин, {Григорий Павлович} and Глушакова, {Дарья Валерьевна} and Шаройко, {Владимир Владимирович} and Красавин, {Михаил Юрьевич}",

year = "2023",

month = jan,

day = "5",

doi = "10.1021/acs.joc.2c02600",

language = "English",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Diazo Tetramic Acids Provide Access to Natural-Like Spirocyclic Δ α,β - Butenolides through Rh(II)-Catalyzed O−H Insertion/Base-Promoted Cyclization

AU - Дарьин, Дмитрий Викторович

AU - Кантин, Григорий Павлович

AU - Глушакова, Дарья Валерьевна

AU - Шаройко, Владимир Владимирович

AU - Красавин, Михаил Юрьевич

PY - 2023/1/5

Y1 - 2023/1/5

N2 - 3-Diazotetramic acids were found to be validsubstrates for the recently discovered approach toward natural-like Δ α,β -spirobutenolides via Rh(II)-catalyzed O−H insertion intopropiolic acids followed by base-promoted intramolecular Michaeladdition. The target Δ α,β -spirobutenolides were obtained ingenerally high yields and, in the case of chiral 5-monosubstituted3-diazotetramic acids, high diastereoselectivity. The synthesis ofΔ α,β -spirobutenolides that we report here was virtually insensitiveto the structure of the propiolic acids though it was somewhat sensitive to the structure of the 3-diazotetramic acids, therebydemonstrating quite a large scope. Thus, a new class of α-diazocarbonyl compounds suitable for the realization of the approachoutlined above was identified.

AB - 3-Diazotetramic acids were found to be validsubstrates for the recently discovered approach toward natural-like Δ α,β -spirobutenolides via Rh(II)-catalyzed O−H insertion intopropiolic acids followed by base-promoted intramolecular Michaeladdition. The target Δ α,β -spirobutenolides were obtained ingenerally high yields and, in the case of chiral 5-monosubstituted3-diazotetramic acids, high diastereoselectivity. The synthesis ofΔ α,β -spirobutenolides that we report here was virtually insensitiveto the structure of the propiolic acids though it was somewhat sensitive to the structure of the 3-diazotetramic acids, therebydemonstrating quite a large scope. Thus, a new class of α-diazocarbonyl compounds suitable for the realization of the approachoutlined above was identified.

UR - https://www.mendeley.com/catalogue/22e7455c-adf5-3f86-beba-2d232f513463/

U2 - 10.1021/acs.joc.2c02600

DO - 10.1021/acs.joc.2c02600

M3 - Article

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -

ID: 113685807