Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

Jiashen Qiu; Di Wu; Lexia Yuan; Pingliang Long; Hongquan Yin; Fuxue Chen

doi:10.1021/acs.joc.9b00782

Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

Jiashen Qiu
, Di Wu
, Lexia Yuan
, Pingliang Long
, 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

43 Citations (Scopus)

Abstract

An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99%) and good enantioselectivities (up to 6:94 er).

Original language	English
Pages (from-to)	7917-7926
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	84
Issue number	12
DOIs	https://doi.org/10.1021/acs.joc.9b00782
Publication status	Published - 21 Jun 2019

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title = "Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles",

abstract = "An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99\%) and good enantioselectivities (up to 6:94 er).",

author = "Jiashen Qiu and Di Wu and Lexia Yuan and Pingliang Long and Hongquan Yin and Fuxue Chen",

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

year = "2019",

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day = "21",

doi = "10.1021/acs.joc.9b00782",

language = "English",

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T1 - Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles

T2 - Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

AU - Qiu, Jiashen

AU - Wu, Di

AU - Yuan, Lexia

AU - Long, Pingliang

AU - Yin, Hongquan

AU - Chen, Fuxue

PY - 2019/6/21

Y1 - 2019/6/21

N2 - An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99%) and good enantioselectivities (up to 6:94 er).

AB - An enantioselective thiocyanation of oxindoles has been developed for the first time using a bifunctional cinchona-derived organo-catalyst and N-thiocyanatophthalimide as the electrophilic thiocyanation source in the presence of 2-naphthol as the additive. Various enantioenriched 3,3′-disubstituted oxindoles with SCN-containing quaternary carbon stereocenters were synthesized under mild conditions in high yields (up to 99%) and good enantioselectivities (up to 6:94 er).

UR - https://www.scopus.com/pages/publications/85067664628

U2 - 10.1021/acs.joc.9b00782

DO - 10.1021/acs.joc.9b00782

M3 - Article

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AN - SCOPUS:85067664628

SN - 0022-3263

VL - 84

SP - 7917

EP - 7926

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

Organocatalyzed Asymmetric α-Thiocyanation of Oxindoles: Synthesis of Chiral Tertiary 3-Thiocyanatoxindoles

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