Stereoselective organozinc addition reactions to 1,2-dihydropyrans for the assembly of complex pyran structures.
[reaction: see text] Nucleophilic addition of organozincs to 1,2-dihydropyranyl acetates represents a new, broadly defined method for the stereocontrolled synthesis of alpha-substituted pyrans. The products obtained from this process are versatile materials that can be used to construct C-glycosides and other functionalized pyran structures of import. The occurrence of pyranyl groups in both natural products and therapeutically active agents confers added value to the studies described herein.
Steinhuebel
Dietrich P
DP
Department of Chemistry, Stanford University, Stanford, California 94305, USA.
Fleming
James J
JJ
Du Bois
J
J
D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D009942:Organometallic Compounds; D011714:Pyrans; D015032:Zinc