Diastereoselective synthesis and spin-dependent photodecarbonylation of di(3-phenyl-2-pyrrolidinon-3-yl)ketones: synthesis of nonadjacent and adjacent stereogenic quaternary centers.
A diastereoselective procedure to obtain N-para-methoxybenzyl bis-alpha,alpha'-3-(3-phenyl-2-pyrrolidinone)yl substituted ketones with non-adjacent quaternary stereocenters, DL-2 and meso-3 was followed by a photoinduced, spin-dependent, and diastereoselective decarbonylation to give compounds DL-4 and meso-5, with adjacent all-carbon quaternary stereogenic centers.
Resendiz
Marino J E
MJ
Department of Chemistry and Biochemistry, University of California-Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA.
Natarajan
Arunkumar
A
Garcia-Garibay
Miguel A
MA
D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010777:Photochemistry; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D011759:Pyrrolidines; D002244:Carbon