Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene

Pran Gopal Karmaker; Jiashen Qiu; Di Wu; Sule Zhang; Hongquan Yin; Fu Xue Chen

doi:10.1016/j.tetlet.2018.04.032

Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene

Pran Gopal Karmaker
, Jiashen Qiu
, Di Wu
, Sule Zhang
, 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

6 引用（Scopus）

摘要

By using a readily accessible, new and safe cyano-transfer reagent, 1-cyanato-4-nitrobenzene, the enantioselectivity of the direct electrophilic α-cyanation of 1-indanone-derived β-keto amides was greatly improved as a result of an enhanced double-hydrogen bonding. Thus, in the presence of cinchonine as the bifunctional organocatalyst, a series of α-cyano β-keto amides were produced in excellent yields (73–97%) and good to high enantioselectivities (75–91% ee) under mild reaction conditions.

源语言	英语
页（从-至）	2034-2037
页数	4
期刊	Tetrahedron Letters
卷	59
期	21
DOI	https://doi.org/10.1016/j.tetlet.2018.04.032
出版状态	已出版 - 23 5月 2018

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10.1016/j.tetlet.2018.04.032

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@article{1a8e995599d445e5a602588728a415e6,

title = "Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene",

abstract = "By using a readily accessible, new and safe cyano-transfer reagent, 1-cyanato-4-nitrobenzene, the enantioselectivity of the direct electrophilic α-cyanation of 1-indanone-derived β-keto amides was greatly improved as a result of an enhanced double-hydrogen bonding. Thus, in the presence of cinchonine as the bifunctional organocatalyst, a series of α-cyano β-keto amides were produced in excellent yields (73–97\%) and good to high enantioselectivities (75–91\% ee) under mild reaction conditions.",

keywords = "Asymmetric catalysis, Cinchona alkaloids, Nitriles, Organocatalysis, β-Ketoamides",

author = "Karmaker, \{Pran Gopal\} and Jiashen Qiu and Di Wu and Sule Zhang and Hongquan Yin and Chen, \{Fu Xue\}",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = may,

day = "23",

doi = "10.1016/j.tetlet.2018.04.032",

language = "English",

volume = "59",

pages = "2034--2037",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene

AU - Karmaker, Pran Gopal

AU - Qiu, Jiashen

AU - Wu, Di

AU - Zhang, Sule

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2018/5/23

Y1 - 2018/5/23

N2 - By using a readily accessible, new and safe cyano-transfer reagent, 1-cyanato-4-nitrobenzene, the enantioselectivity of the direct electrophilic α-cyanation of 1-indanone-derived β-keto amides was greatly improved as a result of an enhanced double-hydrogen bonding. Thus, in the presence of cinchonine as the bifunctional organocatalyst, a series of α-cyano β-keto amides were produced in excellent yields (73–97%) and good to high enantioselectivities (75–91% ee) under mild reaction conditions.

AB - By using a readily accessible, new and safe cyano-transfer reagent, 1-cyanato-4-nitrobenzene, the enantioselectivity of the direct electrophilic α-cyanation of 1-indanone-derived β-keto amides was greatly improved as a result of an enhanced double-hydrogen bonding. Thus, in the presence of cinchonine as the bifunctional organocatalyst, a series of α-cyano β-keto amides were produced in excellent yields (73–97%) and good to high enantioselectivities (75–91% ee) under mild reaction conditions.

KW - Asymmetric catalysis

KW - Cinchona alkaloids

KW - Nitriles

KW - Organocatalysis

KW - β-Ketoamides

UR - https://www.scopus.com/pages/publications/85045710865

U2 - 10.1016/j.tetlet.2018.04.032

DO - 10.1016/j.tetlet.2018.04.032

M3 - Article

AN - SCOPUS:85045710865

SN - 0040-4039

VL - 59

SP - 2034

EP - 2037

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene

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