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Umpolung Strategy for the One-Pot Synthesis of Highly Steric Bispirooxindoles via the l-Amino Acid Ester-Promoted In Situ Reduction/Nucleophilic Addition/Cyclization Cascade Reaction.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2024 Sep 06; Vol. 89 (17), pp. 12716-12724. Date of Electronic Publication: 2024 Aug 13. - Publication Year :
- 2024
-
Abstract
- On the basis of a novel umpolung strategy, an efficient l-amino acid ester-mediated in situ reduction of 2-(2-oxoindolin-3-ylidene)malononitrile and sequential nucleophilic addition/cyclization cascade reaction is reported. Various densely substituted cyclopentene bispirooxindoles and dihydrofuran bispirooxindoles with two quaternary spirocenters were constructed in high yields (≤93%) with excellent diastereoselectivities (>20:1 dr). The method has advantages of readily available starting materials, mild reaction conditions, a one-pot process, a metal-free biomimetic reducing agent, a wide substrate scope, and operational simplicity (single filtration without column chromatography).
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 89
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39138971
- Full Text :
- https://doi.org/10.1021/acs.joc.4c00965