Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

Jiashen Qiu; Di Wu; Pran Gopal Karmaker; Guirong Qi; Peng Chen; Hongquan Yin; Fuxue 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, Fuxue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

38 Citations (Scopus)

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 Å MS and 2,6-lutidine in THF at 0 °C.

Original language	English
Pages (from-to)	4018-4021
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.7b01756
Publication status	Published - 4 Aug 2017

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title = "Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles",

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 Fuxue Chen",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.orglett.7b01756",

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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, Fuxue

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.

UR - https://www.scopus.com/pages/publications/85027028385

U2 - 10.1021/acs.orglett.7b01756

DO - 10.1021/acs.orglett.7b01756

M3 - Article

C2 - 28726413

AN - SCOPUS:85027028385

SN - 1523-7060

VL - 19

SP - 4018

EP - 4021

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

Abstract

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