Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step.
A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids. It has also been shown that the obtained pyrrolines can be efficiently transformed into the corresponding saturated 5-aryl-substituted proline derivatives.
van Esseveldt
Bart C J
BC
Radboud University Nijmegen, Institute for Molecules and Materials, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.
Vervoort
Paul W H
PW
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
C499756:RP 66803; D012834:Silver; D011392:Proline