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

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...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2022; no. 26
Main Authors Niu, Cheng, Du, Da‐Ming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 14.07.2022
Subjects
1,3-Dipolar cycloaddition
Asymmetric catalysis
Benzothiophenones
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Synthetic methods
Trifluoroethyl ketimines
1
Benzothiophenones
ENANTIOSELECTIVE SYNTHESIS
3-Dipolar cycloaddition
Trifluoroethyl ketimines
Synthetic methods
Asymmetric catalysis
DERIVATIVES
SPIROOXINDOLES
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Summary: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). An efficient and mild method to access CF3‐containing bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s is reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200645