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One-Carbon Homologation of Knoevenagel Adducts: Enantioselective Access to Benzhydryl Derivatives
- Source :
- The Journal of Organic Chemistry; May 2024, Vol. 89 Issue: 10 p7270-7274, 5p
- Publication Year :
- 2024
-
Abstract
- A one-carbon homologation of Knoevenagel adducts enabling the insertion of a CHAr fragment is reported. The strategy involves a sulfur ylide mediated cyclopropanation followed by the rearrangement of cyclopropanes and enables the synthesis of a series of benzhydryl derivatives. Mechanistic studies reveal that the cyclopropane rearrangement involves a Lewis acid catalyzed ring-opening followed by the 1,2-migration of an aryl group. The possibility of controlling the absolute stereochemistry of the generated stereogenic allylic carbon center using a chiral sulfonium ylide is demonstrated.
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 89
- Issue :
- 10
- Database :
- Supplemental Index
- Journal :
- The Journal of Organic Chemistry
- Publication Type :
- Periodical
- Accession number :
- ejs66396453
- Full Text :
- https://doi.org/10.1021/acs.joc.4c00057