Regioselective Rh-catalyzed allylic amination/ring-closing metathesis approach to monocyclic azacycles: diastereospecific construction of 2,5-disubstituted pyrrolines.
[formula: see text] Regioselective rhodium-catalyzed allylic amination followed by ring-closing metathesis, using the Grubbs' catalyst, provides an expeditious route to monosubstituted azacycles. The enantiomerically enriched allylamine 1 can also be resubjected to the reaction sequence with (R)- and (S)-2b to facilitate the diastereospecific construction of 2,5-disubstituted pyrrolines 3/4.
Evans
P A
PA
Brown Laboratory, Department of Chemistry and Biochemistry, University of Delaware, Newark 19716, USA. paevans@udel.edu
Robinson
J E
JE
D000586:Amination; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D011758:Pyrroles / Q000737:chemistry*; D012238:Rhodium; D013237:Stereoisomerism
D001372:Aza Compounds; D011758:Pyrroles; D012238:Rhodium