Organocatalyzed asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans and N-2,2,2-trifluoroethylisatin ketimines.
Chirality
; 34(7): 1019-1034, 2022 07.
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| MEDLINE
| ID: mdl-35521642
ABSTRACT
A readily available chiral cyclohexanediamine-derived bifunctional tertiary amine-squaramide catalyst is more effective for the asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans and N-2,2,2-trifluoroethylisatin ketimines. A range of structurally diverse spiro-fused polyheterocyclic compounds containing oxindole, pyrrolidine, and hydrobenzofuran motifs were smoothly obtained in excellent results (up to 99% yield, >201 dr in all cases and up to 99% ee). This method features high efficiency, mild reaction conditions, exquisite asymmetric induction, wide functional group tolerance, great potential for scale-up synthesis, and attractive product diversification.
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Compuestos de Espiro
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Chirality
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BIOLOGIA MOLECULAR
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QUIMICA
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2022
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Article