Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

Jiashen Qiu; Di Wu; Pran Gopal Karmaker; Guirong Qi; Peng Chen; Hongquan Yin; Fu Xue Chen

doi:10.1021/acs.orglett.7b01756

Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

Jiashen Qiu, Di Wu, Pran Gopal Karmaker, Guirong Qi, Peng Chen, 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

34 引用（Scopus）

摘要

The first example of catalytic asymmetric electrophilic cyanation of 3-substituted oxindoles has been achieved using readily accessible 4-acetylphenyl cyanate as the cyano source. Thus, a series of all-carbon quaternary center 3-aryl-3-cyano oxindoles were prepared using a zinc complex of a chiral pincer ligand as the catalyst in high yields (up to 95%) and excellent enantioselectivities (up to >99% ee) in the presence of 4 Å MS and 2,6-lutidine in THF at 0 °C.

源语言	英语
页（从-至）	4018-4021
页数	4
期刊	Organic Letters
卷	19
期	15
DOI	https://doi.org/10.1021/acs.orglett.7b01756
出版状态	已出版 - 4 8月 2017

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abstract = "The first example of catalytic asymmetric electrophilic cyanation of 3-substituted oxindoles has been achieved using readily accessible 4-acetylphenyl cyanate as the cyano source. Thus, a series of all-carbon quaternary center 3-aryl-3-cyano oxindoles were prepared using a zinc complex of a chiral pincer ligand as the catalyst in high yields (up to 95%) and excellent enantioselectivities (up to >99% ee) in the presence of 4 {\AA} MS and 2,6-lutidine in THF at 0 °C.",

author = "Jiashen Qiu and Di Wu and Karmaker, {Pran Gopal} and Guirong Qi and Peng Chen and Hongquan Yin and Chen, {Fu Xue}",

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T1 - Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

AU - Qiu, Jiashen

AU - Wu, Di

AU - Karmaker, Pran Gopal

AU - Qi, Guirong

AU - Chen, Peng

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2017/8/4

Y1 - 2017/8/4

N2 - The first example of catalytic asymmetric electrophilic cyanation of 3-substituted oxindoles has been achieved using readily accessible 4-acetylphenyl cyanate as the cyano source. Thus, a series of all-carbon quaternary center 3-aryl-3-cyano oxindoles were prepared using a zinc complex of a chiral pincer ligand as the catalyst in high yields (up to 95%) and excellent enantioselectivities (up to >99% ee) in the presence of 4 Å MS and 2,6-lutidine in THF at 0 °C.

AB - The first example of catalytic asymmetric electrophilic cyanation of 3-substituted oxindoles has been achieved using readily accessible 4-acetylphenyl cyanate as the cyano source. Thus, a series of all-carbon quaternary center 3-aryl-3-cyano oxindoles were prepared using a zinc complex of a chiral pincer ligand as the catalyst in high yields (up to 95%) and excellent enantioselectivities (up to >99% ee) in the presence of 4 Å MS and 2,6-lutidine in THF at 0 °C.

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SP - 4018

EP - 4021

JO - Organic Letters

JF - Organic Letters

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Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

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