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^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2034-2037
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2018.04.032
Publication status	Published - 23 May 2018

Keywords

Asymmetric catalysis
Cinchona alkaloids
Nitriles
Organocatalysis
β-Ketoamides

Access to Document

10.1016/j.tetlet.2018.04.032

Cite this

@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",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "21",

}

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 - http://www.scopus.com/inward/record.url?scp=85045710865&partnerID=8YFLogxK

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this