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Asymmetric Cascade Aza-Henry/Lactamization Reaction in the Highly Enantioselective Organocatalytic Synthesis of 3-(Nitromethyl)isoindolin-1-ones from α-Amido Sulfones.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2022 Jul 01; Vol. 87 (13), pp. 8420-8428. Date of Electronic Publication: 2022 Jun 14. - Publication Year :
- 2022
-
Abstract
- The asymmetric synthesis of novel 3-substituted isoindolinones is herein reported. A new cascade reaction was developed that consisted of the asymmetric nitro-Mannich reaction of suitable α-amido sulfones designed from 2-formyl benzoates, followed by the in situ cyclization of the adducts. Very high enantioselectivities, up to 98% ee, and very good yields were obtained in the presence of the readily available neutral bifunctional organocatalyst derived from trans -1,2-diaminocyclohexane, which is known as Takemoto's catalyst. The investigation of the reactivity of the obtained products allowed either the selective Boc-deprotection or reduction of the nitro group, leading to further functionalized 3-substituted isoindolinones without affecting the enantiomeric purity.
- Subjects :
- Catalysis
Cyclization
Molecular Structure
Stereoisomerism
Sulfones
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 87
- Issue :
- 13
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 35699594
- Full Text :
- https://doi.org/10.1021/acs.joc.2c00518