European Journal of Organic Chemistry

, том 2013 , издание 12 , страницы 2453-2460

Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes

Тип публикации: Journal Article

Дата публикации: 2013-03-11

Wiley

European Journal of Organic Chemistry

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SJR: 0.558

CiteScore: 4.3

Impact factor: 2.7

ISSN: 1434193X, 10990690

DOI: 10.1002/ejoc.201201700

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Organic Chemistry

Physical and Theoretical Chemistry

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1,5-Diketones are readily cyclized in the presence of various alkali-metal superbases with acetylenes at 70 °C in a one-pot cascade reaction to give methylene-6,8-dioxabicyclo[3.2.1]octanes in up to 92 % yield. In the case of symmetrical 1,5-diketones, only one diastereomer is formed, whereas unsymmetrical diketones afford two diastereomers in a ratio corresponding to that of the starting ketones. This result indicates the key cascade cyclization sequence is stereoselective.

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Schmidt E. Yu. et al. Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes // European Journal of Organic Chemistry. 2013. Vol. 2013. No. 12. pp. 2453-2460.

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Schmidt E. Yu., Bidusenko I. A., Protsuk N. I., Ushakov I., Trofimov B. A. Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes // European Journal of Organic Chemistry. 2013. Vol. 2013. No. 12. pp. 2453-2460.

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TY - JOUR

DO - 10.1002/ejoc.201201700

UR - https://doi.org/10.1002/ejoc.201201700

TI - Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes

T2 - European Journal of Organic Chemistry

AU - Schmidt, Elena Yu

AU - Bidusenko, Ivan A

AU - Protsuk, Nadezhda I

AU - Ushakov, Igor

AU - Trofimov, B. A.

PY - 2013

DA - 2013/03/11

PB - Wiley

SP - 2453-2460

IS - 12

VL - 2013

SN - 1434-193X

SN - 1099-0690

ER -

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@article{2013_Schmidt,

author = {Elena Yu Schmidt and Ivan A Bidusenko and Nadezhda I Protsuk and Igor Ushakov and B. A. Trofimov},

title = {Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes},

journal = {European Journal of Organic Chemistry},

year = {2013},

volume = {2013},

publisher = {Wiley},

month = {mar},

url = {https://doi.org/10.1002/ejoc.201201700},

number = {12},

pages = {2453--2460},

doi = {10.1002/ejoc.201201700}

}

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Schmidt, Elena Yu., et al. “Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes.” European Journal of Organic Chemistry, vol. 2013, no. 12, Mar. 2013, pp. 2453-2460. https://doi.org/10.1002/ejoc.201201700.