Organic Letters

, том 21 , издание 20 , страницы 8196-8200

Catalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations

Тип публикации: Journal Article

Дата публикации: 2019-10-01

American Chemical Society (ACS)

Organic Letters

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SJR: 1.007

CiteScore: 7.7

Impact factor: 4.7

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.9b02852

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PubMed ID: 31573211

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

We report a scandium-catalyzed [3 + 2] annulation of alkylideneoxindoles with allenylsilanes for the enantioselective formation of cyclopentene-spirooxindoles containing vinylsilanes. Using a Sc(OTf)2/PyBOX/BArF complex, the spiroannulation of allenylsilanes affords products with >94:6 dr and >90:10 er. The effect of the counterion and ligand to control selectivity is discussed. The transformation of the vinylsilane is demonstrated using cross-coupling, epoxidation, and Tamao-Fleming oxidation reactions. A series of competition experiments provide a comparison of nucleophilicity between allyl- and allenylsilanes.

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Organic Chemistry Frontiers	Organic Chemistry Frontiers, 4, 30.77% Organic Chemistry Frontiers 4 публикации, 30.77%
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Cobos A. et al. Catalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations // Organic Letters. 2019. Vol. 21. No. 20. pp. 8196-8200.

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Cobos A., Armstrong B. M., Fettinger J. C., Franz A. K. Catalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations // Organic Letters. 2019. Vol. 21. No. 20. pp. 8196-8200.

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TY - JOUR

DO - 10.1021/acs.orglett.9b02852

UR - https://doi.org/10.1021/acs.orglett.9b02852

TI - Catalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations

T2 - Organic Letters

AU - Cobos, Angel

AU - Armstrong, Brittany M

AU - Fettinger, James C.

AU - Franz, Annaliese K

PY - 2019

DA - 2019/10/01

PB - American Chemical Society (ACS)

SP - 8196-8200

IS - 20

VL - 21

PMID - 31573211

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2019_Cobos,

author = {Angel Cobos and Brittany M Armstrong and James C. Fettinger and Annaliese K Franz},

title = {Catalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations},

journal = {Organic Letters},

year = {2019},

volume = {21},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://doi.org/10.1021/acs.orglett.9b02852},

number = {20},

pages = {8196--8200},

doi = {10.1021/acs.orglett.9b02852}

}

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Cobos, Angel, et al. “Catalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations.” Organic Letters, vol. 21, no. 20, Oct. 2019, pp. 8196-8200. https://doi.org/10.1021/acs.orglett.9b02852.

Издатель

American Chemical Society (ACS)

Журнал

Organic Letters

SCImago Q1

Tоп 10% SCImago

WOS Q1

БС1