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A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2016 Jul 06; Vol. 14 (27), pp. 6457-62. - Publication Year :
- 2016
-
Abstract
- We report a diastereoselective Mannich-type reaction of α-alkyl, α-aryl, and α-vinyl fluoroacetates with N-tert-butylsulfinyl imines. This method provides a powerful means to access a broad range of highly functionalized β-amino acids containing α-fluorinated quaternary stereogenic carbon centers. We also show that the stereochemical outcome of the present reaction is highly dependent on the steric and electronic properties of the fluorocarbon nucleophiles. This protocol uses readily available starting materials, tolerates a variety of functional groups, and is operationally simple.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 14
- Issue :
- 27
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27279124
- Full Text :
- https://doi.org/10.1039/c6ob01084a