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^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

3 Citations (Scopus)

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).

Original language	English
Article number	e202200645
Journal	European Journal of Organic Chemistry
Volume	2022
Issue number	26
DOIs	https://doi.org/10.1002/ejoc.202200645
Publication status	Published - 14 Jul 2022

Keywords

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

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10.1002/ejoc.202200645

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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}",

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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

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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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Keywords

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