Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.
Dihydropyran derivatives readily undergo addition to N-acyl imines in the presence of chiral phosphoric acids. This addition process yields an attractive product that is capable of a tandem oxidative-cyclization via an epoxide intermediate.
Li
Guilong
G
Department of Chemistry, University of South Florida, 4202 East Fowler Avenue CHE205A, Tampa, Florida 33620, USA.
Kaplan
Matthew J
MJ
Wojtas
Lukasz
L
Antilla
Jon C
JC
D002384:Catalysis; D008958:Models, Molecular; D010756:Phosphoric Acids / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D010756:Phosphoric Acids; D011714:Pyrans; C030242:phosphoric acid