Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

Jiashen Qiu; Di Wu; Lexia Yuan; Pingliang Long; Hongquan Yin; Fu Xue Chen

doi:10.1021/acs.joc.9b00782

Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

Jiashen Qiu, Di Wu, Lexia Yuan, Pingliang Long, Hongquan Yin, Fu Xue Chen^*

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

39 引用（Scopus）

摘要

An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99%) and good enantioselectivities (up to 6:94 er).

源语言	英语
页（从-至）	7917-7926
页数	10
期刊	Journal of Organic Chemistry
卷	84
期	12
DOI	https://doi.org/10.1021/acs.joc.9b00782
出版状态	已出版 - 21 6月 2019

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abstract = "An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99%) and good enantioselectivities (up to 6:94 er).",

author = "Jiashen Qiu and Di Wu and Lexia Yuan and Pingliang Long and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.joc.9b00782",

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T1 - Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles

T2 - Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

AU - Qiu, Jiashen

AU - Wu, Di

AU - Yuan, Lexia

AU - Long, Pingliang

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2019/6/21

Y1 - 2019/6/21

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AB - An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99%) and good enantioselectivities (up to 6:94 er).

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JF - Journal of Organic Chemistry

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Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

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