Efficient Synthesis of Chiral β-Seleno Amides via Ring-Opening Reaction of 2-Oxazolines and Their Application in the Palladium-Catalyzed Asymmetric Allylic Alkylation
- 22 September 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (22), 9021-9024
- https://doi.org/10.1021/jo051451a
Abstract
A set of chiral β-seleno amides have been efficiently synthesized via the ring-opening reaction of chiral 2-oxazolines by selenium nucleophiles. The present method is applicable to the synthesis of β-seleno amides containing thioether, alcohol, and ether moieties in good yields. As an application, the synthesis of a selenocysteine derivative has been accomplished. Additionally, these new compounds were evaluated in the palladium-catalyzed asymmetric allylic alkylation, giving the alkylated products in up to 98% ee.Keywords
This publication has 19 references indexed in Scilit:
- Selenium Redox Cycling in the Protective Effects of Organoselenides against Oxidant-Induced DNA DamageJournal of the American Chemical Society, 2004
- Asymmetric Azidoselenenylation of Alkenes: A Key Step for the Synthesis of Enantiomerically Enriched Nitrogen‐Containing CompoundsAngewandte Chemie-International Edition, 2003
- Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total SynthesisChemical Reviews, 2003
- Synthesis of planar chiral selenide derivatives of ferrocenyl-oxazoline and their application in enantioselective palladium catalyzed allylic substitution reactionTetrahedron: Asymmetry, 2000
- (S)-Proline-derived new chiral ligands with phosphino, organosulfur or organoselenenyl functionality as an enantiocontrollable coordinating elementTetrahedron: Asymmetry, 1999
- Synthesis of non-racemic nitrogen-containing diselenides as efficient precursor catalysts in the diethylzinc addition to benzaldehydeTetrahedron: Asymmetry, 1999
- Chiral Diselenides from Benzylamines: Catalysts in the Diethylzinc Addition to AldehydesHelvetica Chimica Acta, 1996
- Total synthesis of westiellamideJournal of the American Chemical Society, 1992
- Structure and behavior of spermidine siderophoresJournal of the American Chemical Society, 1980
- Electro‐Deprotection—Electrochemical Removal of Protecting GroupsAngewandte Chemie-International Edition, 1976