Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

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

doi:10.1021/acs.orglett.8b00342

Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

Jiashen Qiu, Di Wu, Pran Gopal Karmaker, 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

75 引用（Scopus）

摘要

A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.

源语言	英语
页（从-至）	1600-1603
页数	4
期刊	Organic Letters
卷	20
期	6
DOI	https://doi.org/10.1021/acs.orglett.8b00342
出版状态	已出版 - 16 3月 2018

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abstract = "A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.",

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

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b00342",

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T1 - Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

AU - Qiu, Jiashen

AU - Wu, Di

AU - Karmaker, Pran Gopal

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2018/3/16

Y1 - 2018/3/16

N2 - A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.

AB - A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.

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U2 - 10.1021/acs.orglett.8b00342

DO - 10.1021/acs.orglett.8b00342

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

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