Lewis Acid-Catalyzed Asymmetric Selenocyanation of β-Ketoesters with N-Selenocyanatosaccharin

Di Wu; Jiashen Qiu; Chengqiu Li; Lexia Yuan; Hongquan Yin; Fu Xue Chen

doi:10.1021/acs.joc.9b02786

Lewis Acid-Catalyzed Asymmetric Selenocyanation of β-Ketoesters with N-Selenocyanatosaccharin

Di Wu, Jiashen Qiu, Chengqiu Li, Lexia Yuan, 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

25 引用（Scopus）

摘要

The first electrophilic asymmetric selenocyanation has been achieved in the presence of Ni(OTf)₂ and (R,R)-DBFOX/Ph using N-selenocyanatosaccharin as the new selenocyanation reagent. Thus, a series of α-selenocyanato-β-keto esters were synthesized with high yields (up to 99%) and good ee values (up to 92% ee). The readily preparation of the reagent and high enantioselectivity make this methodology much practical for the synthesis of chiral selenocyanates.

源语言	英语
页（从-至）	934-941
页数	8
期刊	Journal of Organic Chemistry
卷	85
期	2
DOI	https://doi.org/10.1021/acs.joc.9b02786
出版状态	已出版 - 17 1月 2020

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title = "Lewis Acid-Catalyzed Asymmetric Selenocyanation of β-Ketoesters with N-Selenocyanatosaccharin",

abstract = "The first electrophilic asymmetric selenocyanation has been achieved in the presence of Ni(OTf)2 and (R,R)-DBFOX/Ph using N-selenocyanatosaccharin as the new selenocyanation reagent. Thus, a series of α-selenocyanato-β-keto esters were synthesized with high yields (up to 99%) and good ee values (up to 92% ee). The readily preparation of the reagent and high enantioselectivity make this methodology much practical for the synthesis of chiral selenocyanates.",

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

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T1 - Lewis Acid-Catalyzed Asymmetric Selenocyanation of β-Ketoesters with N-Selenocyanatosaccharin

AU - Wu, Di

AU - Qiu, Jiashen

AU - Li, Chengqiu

AU - Yuan, Lexia

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2020/1/17

Y1 - 2020/1/17

N2 - The first electrophilic asymmetric selenocyanation has been achieved in the presence of Ni(OTf)2 and (R,R)-DBFOX/Ph using N-selenocyanatosaccharin as the new selenocyanation reagent. Thus, a series of α-selenocyanato-β-keto esters were synthesized with high yields (up to 99%) and good ee values (up to 92% ee). The readily preparation of the reagent and high enantioselectivity make this methodology much practical for the synthesis of chiral selenocyanates.

AB - The first electrophilic asymmetric selenocyanation has been achieved in the presence of Ni(OTf)2 and (R,R)-DBFOX/Ph using N-selenocyanatosaccharin as the new selenocyanation reagent. Thus, a series of α-selenocyanato-β-keto esters were synthesized with high yields (up to 99%) and good ee values (up to 92% ee). The readily preparation of the reagent and high enantioselectivity make this methodology much practical for the synthesis of chiral selenocyanates.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Lewis Acid-Catalyzed Asymmetric Selenocyanation of β-Ketoesters with N-Selenocyanatosaccharin

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