Highly Enantioselective Synthesis of Polycyclic Dihydroisoquinolinones via NHC-Catalyzed [4 + 2] Annulations

The NHC-catalyzed enantioselective [4 + 2] annulation of 9<i>H</i>-fluorene-1-carbaldenydes with cyclic imines was successfully developed. A series of optically enriched polycyclic dihydroisoquinolinones were synthesized in moderate to excellent yields with good to excellent enantioselectivities. In addition, this efficient method could also be amenable to the synthesis of spirocyclic compounds by using isatin-derived ketimines as the electrophiles.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-13
DOI
https://doi.org/10.1021/acs.joc.4c01529
Citations
5
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
1.25

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article

Highly Enantioselective Synthesis of Polycyclic Dihydroisoquinolinones via NHC-Catalyzed [4 + 2] Annulations

Yuxuan Feng, Xiaoyong Duan, Xiaojie Ren, Jiahan Li et al.
5 citations
The Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
1.25
article

Highly Enantioselective Synthesis of Polycyclic Dihydroisoquinolinones via NHC-Catalyzed [4 + 2] Annulations

Yuxuan Feng, Xiaoyong Duan, Xiaojie Ren, Jiahan Li, Jing Qi, Yanting Li
article en
5 citations

Abstract

The NHC-catalyzed enantioselective [4 + 2] annulation of 9<i>H</i>-fluorene-1-carbaldenydes with cyclic imines was successfully developed. A series of optically enriched polycyclic dihydroisoquinolinones were synthesized in moderate to excellent yields with good to excellent enantioselectivities. In addition, this efficient method could also be amenable to the synthesis of spirocyclic compounds by using isatin-derived ketimines as the electrophiles.

The Journal of Organic ChemistryVol. 89(19)
Hebei University (CN)
Natural Science Foundation of Hebei Province, Hebei University
Openalex Percentile: Top 23%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
1.25
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