Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.
Palladium-catalyzed carboamination reactions between aryl bromides and 4-(but-3-enyl)-substituted oxazolidin-2-ones are described. These transformations afford bicyclic oxazolidin-2-one derivatives that can be converted to trans-2,5-disubstituted pyrrolidines in one step. The starting materials are easily prepared from amino acid precursors, and products that contain up to three stereocenters are generated with >20:1 dr.
Lemen
Georgia S
GS
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Wolfe
John P
JP
D000586:Amination; D002384:Catalysis; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009942:Organometallic Compounds; D023303:Oxazolidinones; D011759:Pyrrolidines; D010165:Palladium
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