, volume 24 , issue 16 , pages 3064-3068

Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes

Yanfeng Gao ¹

Yuanhao Mao ¹

Zhiwei Miao ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Weijin Road 94, Tianjin 300071, China |

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China |

Publication type: Journal Article

Publication date: 2022-04-14

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.2c01037

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PubMed ID: 35420826

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

We have developed an efficient and mild enantioselective palladium-catalyzed (5+3) cycloaddition of vinylcyclopropanes and oxidopyrylium ylides generated in situ from benzopyranones, in the presence of a chiral PHOX ligand. These reactions afford various highly functionalized bridged oxa-[3.3.1]carbocycles with three stereogenic centers that are challenging to synthesize, in moderate to good yields and enantioselectivities.

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N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Peoples' Friendship University of Russia

1 citation

Andreev Ivan

PhD in Chemistry

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h-index: 12

Peoples' Friendship University of Russia

Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

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Antonova Yulia

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h-index: 3

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

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Sedov Igor

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h-index: 22

Kazan Federal University

Sirius University of Science and Technology

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Gao Y. et al. Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes // Organic Letters. 2022. Vol. 24. No. 16. pp. 3064-3068.

GOST all authors (up to 50) Copy

Gao Y., Mao Y., Miao Z. Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes // Organic Letters. 2022. Vol. 24. No. 16. pp. 3064-3068.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.2c01037

UR - https://doi.org/10.1021/acs.orglett.2c01037

TI - Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes

T2 - Organic Letters

AU - Gao, Yanfeng

AU - Mao, Yuanhao

AU - Miao, Zhiwei

PY - 2022

DA - 2022/04/14

PB - American Chemical Society (ACS)

SP - 3064-3068

IS - 16

VL - 24

PMID - 35420826

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2022_Gao,

author = {Yanfeng Gao and Yuanhao Mao and Zhiwei Miao},

title = {Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes},

journal = {Organic Letters},

year = {2022},

volume = {24},

publisher = {American Chemical Society (ACS)},

month = {apr},

url = {https://doi.org/10.1021/acs.orglett.2c01037},

number = {16},

pages = {3064--3068},

doi = {10.1021/acs.orglett.2c01037}

}

MLA

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MLA Copy

Gao, Yanfeng, et al. “Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes.” Organic Letters, vol. 24, no. 16, Apr. 2022, pp. 3064-3068. https://doi.org/10.1021/acs.orglett.2c01037.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)