title: Silyl enol ether Prins cyclization: diastereoselective formation of substituted tetrahydropyran-4-ones.
abstract: A diastereoselective synthesis of cis-2,6-disubstituted tetrahydropyran-4-ones was developed. The key step of this methodology, a silyl enol ether Prins cyclization, was promoted by a condensation reaction between a hydroxy silyl enol ether and an aldehyde to afford substituted tetrahydropyran-4-ones. The cyclization was tolerant of many functional groups, and the modular synthesis of the hydroxy silyl enol ether allowed for the formation of more than 30 new tetrahydropyran-4-ones with up to 97% yield and >95:5 dr. The cyclization step forms new carbon-carbon and carbon-oxygen bonds, as well as a quaternary center with good diastereoselectivity. The method provides a versatile route for the synthesis of substituted tetrahydropyrans.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine , Irvine, California 92697, United States.
authors.forename: Gidget C
authors.initials: GC
authors.lastname: Tay
authors.forename: Chloe Y
authors.initials: CY
authors.lastname: Huang
authors.forename: Scott D
authors.initials: SD
authors.lastname: Rychnovsky
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004987:Ethers; D017646:Organosilicon Compounds; D011714:Pyrans