Diastereoselective Construction of CF3-Containing Bispiro[isoquinolone-pyrrolidine-benzothiophenone]s through 1,3-Dipolar Cycloaddition

Cheng Niu; Da Ming Du

doi:10.1002/ejoc.202200645

Diastereoselective Construction of CF₃-Containing Bispiro[isoquinolone-pyrrolidine-benzothiophenone]s through 1,3-Dipolar Cycloaddition

Cheng Niu
, Da Ming Du^*

^*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

3 引用（Scopus）

摘要

A new protocol to access CF₃-containing bispiro[isoquinolone-pyrrolidine-benzothiophenone]s was described. A series of 1,3-dipoles were synthesized from isoquinolinetrione and CF₃CH₂NH₂. In the presence of 10 mol% DABCO, the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 %) and diastereoselectivities (up to >20 : 1 dr).

源语言	英语
文章编号	e202200645
期刊	European Journal of Organic Chemistry
卷	2022
期	26
DOI	https://doi.org/10.1002/ejoc.202200645
出版状态	已出版 - 14 7月 2022

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@article{2cfa0624867e464cbcd1dbb4d0e9c842,

title = "Diastereoselective Construction of CF3-Containing Bispiro[isoquinolone-pyrrolidine-benzothiophenone]s through 1,3-Dipolar Cycloaddition",

abstract = "A new protocol to access CF3-containing bispiro[isoquinolone-pyrrolidine-benzothiophenone]s was described. A series of 1,3-dipoles were synthesized from isoquinolinetrione and CF3CH2NH2. In the presence of 10 mol\% DABCO, the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 \%) and diastereoselectivities (up to >20 : 1 dr).",

keywords = "1,3-Dipolar cycloaddition, Asymmetric catalysis, Benzothiophenones, Synthetic methods, Trifluoroethyl ketimines",

author = "Cheng Niu and Du, \{Da Ming\}",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jul,

day = "14",

doi = "10.1002/ejoc.202200645",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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T1 - Diastereoselective Construction of CF3-Containing Bispiro[isoquinolone-pyrrolidine-benzothiophenone]s through 1,3-Dipolar Cycloaddition

AU - Niu, Cheng

AU - Du, Da Ming

PY - 2022/7/14

Y1 - 2022/7/14

N2 - A new protocol to access CF3-containing bispiro[isoquinolone-pyrrolidine-benzothiophenone]s was described. A series of 1,3-dipoles were synthesized from isoquinolinetrione and CF3CH2NH2. In the presence of 10 mol% DABCO, the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 %) and diastereoselectivities (up to >20 : 1 dr).

AB - A new protocol to access CF3-containing bispiro[isoquinolone-pyrrolidine-benzothiophenone]s was described. A series of 1,3-dipoles were synthesized from isoquinolinetrione and CF3CH2NH2. In the presence of 10 mol% DABCO, the 1,3-dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 %) and diastereoselectivities (up to >20 : 1 dr).

KW - 1,3-Dipolar cycloaddition

KW - Asymmetric catalysis

KW - Benzothiophenones

KW - Synthetic methods

KW - Trifluoroethyl ketimines

UR - https://www.scopus.com/pages/publications/85134027036

U2 - 10.1002/ejoc.202200645

DO - 10.1002/ejoc.202200645

M3 - Article

AN - SCOPUS:85134027036

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 26

M1 - e202200645

ER -

Diastereoselective Construction of CF3-Containing Bispiro[isoquinolone-pyrrolidine-benzothiophenone]s through 1,3-Dipolar Cycloaddition

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Diastereoselective Construction of CF₃-Containing Bispiro[isoquinolone-pyrrolidine-benzothiophenone]s through 1,3-Dipolar Cycloaddition