Pt-catalyzed tandem epoxide fragmentation/pentannulation of propargylic esters.
A Pt-catalyzed pentannulation of propargylic esters containing an epoxide moiety has been developed. The present transformation achieves the formation of cyclopentenone products as single diastereomers in good yields. The observed products likely form from pyran intermediates that undergo an oxa-6pi electrocyclic ring opening to a functionalized dienone, followed by ring closure with an accompanying acyl shift.
Pujanauski
Brian G
BG
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Bhanu Prasad
B A
BA
Sarpong
Richmond
R
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D010984:Platinum / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D004952:Esters; D011714:Pyrans; D010984:Platinum