Journal of Organic Chemistry

, том 86 , издание 23 , страницы 17119-17128

Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary

Тип публикации: Journal Article

Дата публикации: 2021-11-12

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.1c02241

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PubMed ID: 34766772

Organic Chemistry

Краткое описание

Sulfonimidamides (SIAs) and sulfoximines (SOIs) have attracted attention due to their potential in agriculture and in medicinal chemistry as bioisosteres of biologically active compounds, and new synthetic methods are needed to access and explore these compounds. Herein, we present a light-promoted generation of perfluorinated aromatic nitrenes, from perfluorinated azides, that subsequently are allowed to react with sulfinamides and sulfoxides, generating achiral and chiral SIAs and SOIs. One of the enantiopure SIAs was evaluated as a novel chiral auxiliary in Grignard additions to the imines yielding the product in up to 96:4 diastereomeric ratio.

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Proietti G. et al. Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary // Journal of Organic Chemistry. 2021. Vol. 86. No. 23. pp. 17119-17128.

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Proietti G., Kuzmin J., Temerdashev A., Dinér P. Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary // Journal of Organic Chemistry. 2021. Vol. 86. No. 23. pp. 17119-17128.

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TY - JOUR

DO - 10.1021/acs.joc.1c02241

UR - https://doi.org/10.1021/acs.joc.1c02241

TI - Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary

T2 - Journal of Organic Chemistry

AU - Proietti, Giampiero

AU - Kuzmin, Julius

AU - Temerdashev, Azamat

AU - Dinér, Peter

PY - 2021

DA - 2021/11/12

PB - American Chemical Society (ACS)

SP - 17119-17128

IS - 23

VL - 86

PMID - 34766772

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2021_Proietti,

author = {Giampiero Proietti and Julius Kuzmin and Azamat Temerdashev and Peter Dinér},

title = {Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary},

journal = {Journal of Organic Chemistry},

year = {2021},

volume = {86},

publisher = {American Chemical Society (ACS)},

month = {nov},

url = {https://doi.org/10.1021/acs.joc.1c02241},

number = {23},

pages = {17119--17128},

doi = {10.1021/acs.joc.1c02241}

}

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Proietti, Giampiero, et al. “Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary.” Journal of Organic Chemistry, vol. 86, no. 23, Nov. 2021, pp. 17119-17128. https://doi.org/10.1021/acs.joc.1c02241.