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^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

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.

Original language	English
Pages (from-to)	934-941
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	85
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.9b02786
Publication status	Published - 17 Jan 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\}",

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

year = "2020",

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doi = "10.1021/acs.joc.9b02786",

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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.

UR - https://www.scopus.com/pages/publications/85077463195

U2 - 10.1021/acs.joc.9b02786

DO - 10.1021/acs.joc.9b02786

M3 - Article

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SN - 0022-3263

VL - 85

SP - 934

EP - 941

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

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

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