Rhodium(I)-catalyzed cycloisomerizations of bicyclobutanes.
The selection of rhodium precatalyst and phosphine ligand determines the course of the cycloisomerization of N-allylated bicyclo[1.1.0]butylalkylamines. Cyclopropane-fused pyrrolidines and azepines are obtained with high levels of stereo- and regiocontrol. Novel azatricyclo[6.1.0.0(1,5)]nonanes are the result of a tandem cycloisomerization-ring closing metathesis sequence. Allylic ethers lead to furans and oxepanes.
Walczak
Maciej A A
MA
Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, USA.
Wipf
Peter
P
D001381:Azepines / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D007536:Isomerism; D010720:Phosphines / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry*
D001381:Azepines; D001643:Bridged Bicyclo Compounds; D003503:Cyclobutanes; D010720:Phosphines; D011759:Pyrrolidines; D012238:Rhodium