Journal of Organic Chemistry

, том 84 , издание 10 , страницы 6174-6182

Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones

Тип публикации: Journal Article

Дата публикации: 2019-04-17

American Chemical Society (ACS)

Journal of Organic Chemistry

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SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b00354

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PubMed ID: 30994351

Organic Chemistry

Краткое описание

A new cascade three-component process for high trans,trans-diastereoselective assembly of five-membered (1-halovinyl)lactones has been developed. The process is based on reactions of substituted methylidenemalonates and cyclopropanedicarboxylates with 3-haloprop-1-ynes in the presence of GaHal3 and involves the intermediate in situ generation of 1,2-zwitterionic gallium complexes with [Ga(L)3]3+[GaX4-]3 composition. Chloro, bromo, and iodo derivatives can be obtained successfully. Mechanistic and stereochemical aspects of the process we developed have been studied and considered in detail.

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Journal of Organic Chemistry	Journal of Organic Chemistry, 5, 25% Journal of Organic Chemistry 5 публикаций, 25%
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Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 3, 15% Advanced Synthesis and Catalysis 3 публикации, 15%
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Denisov D. A. et al. Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones // Journal of Organic Chemistry. 2019. Vol. 84. No. 10. pp. 6174-6182.

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Denisov D. A., Borisov D. D., Korolev V. A., Novikov R. G., Tomilov Y. V. Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones // Journal of Organic Chemistry. 2019. Vol. 84. No. 10. pp. 6174-6182.

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TY - JOUR

DO - 10.1021/acs.joc.9b00354

UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b00354

TI - Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones

T2 - Journal of Organic Chemistry

AU - Denisov, Dmitry A

AU - Borisov, Denis D

AU - Korolev, Victor A

AU - Novikov, Roman G.

AU - Tomilov, Yury V.

PY - 2019

DA - 2019/04/17

PB - American Chemical Society (ACS)

SP - 6174-6182

IS - 10

VL - 84

PMID - 30994351

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2019_Denisov,

author = {Dmitry A Denisov and Denis D Borisov and Victor A Korolev and Roman G. Novikov and Yury V. Tomilov},

title = {Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {apr},

url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b00354},

number = {10},

pages = {6174--6182},

doi = {10.1021/acs.joc.9b00354}

}

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Denisov, Dmitry A., et al. “Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones.” Journal of Organic Chemistry, vol. 84, no. 10, Apr. 2019, pp. 6174-6182. https://pubs.acs.org/doi/10.1021/acs.joc.9b00354.