Organic Letters

, том 13 , издание 12 , страницы 3068-3071

Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans

Тип публикации: Journal Article

Дата публикации: 2011-05-16

American Chemical Society (ACS)

Organic Letters

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SJR: 1.007

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/ol200940a

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PubMed ID: 21574631

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

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In this paper, a reagent-controlled [3+2] annulation of γ-functionalized butynoates 1 and 1C,3O-bisnucleophiles 2 is reported, which leads to three distinct furan skeletons 3-5. A PPh(3) catalyst preferentially attached the β-position of 1a, facilitating α-addition to furnish Type I annulations. With the assistance of Ag(2)O, Type II annulations were achieved via selective γ-substitution. In the absence of the PPh(3) catalyst, the reagent Cs(2)CO(3) promoted β-addition to realize Type III annulations.

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Hu J., Wei Y., Tong X. Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans // Organic Letters. 2011. Vol. 13. No. 12. pp. 3068-3071.

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TY - JOUR

DO - 10.1021/ol200940a

UR - https://doi.org/10.1021/ol200940a

TI - Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans

T2 - Organic Letters

AU - Hu, Jian

AU - Wei, Yabing

AU - Tong, Xiaofeng

PY - 2011

DA - 2011/05/16

PB - American Chemical Society (ACS)

SP - 3068-3071

IS - 12

VL - 13

PMID - 21574631

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2011_Hu,

author = {Jian Hu and Yabing Wei and Xiaofeng Tong},

title = {Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans},

journal = {Organic Letters},

year = {2011},

volume = {13},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/ol200940a},

number = {12},

pages = {3068--3071},

doi = {10.1021/ol200940a}

}

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Hu, Jian, et al. “Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans.” Organic Letters, vol. 13, no. 12, May. 2011, pp. 3068-3071. https://doi.org/10.1021/ol200940a.

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American Chemical Society (ACS)

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Organic Letters

SCImago Q1

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WOS Q1

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