title: Diastereoselective Prins-type reaction of cycloalkenylcyclopropanol silyl ethers and alpha,beta-unsaturated aldehyde acetals.
abstract: Electrophilic addition of 1-(1-cyclohexenyl)-1-cyclopropanol trimethylsilyl ether to alpha,beta-unsaturated aldehyde acetals under Lewis acidic conditions proceeds with good to excellent diastereoselectivity to afford spirocyclobutanones containing three contiguous stereocenters. A convenient entry to enantioselective syntheses is available by use of a nonracemic C2-symmetric acetal. Elaboration of the resulting adducts provides ready access to medium-sized carbocycles.
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
authors.forename: Ivan L
authors.initials: IL
authors.lastname: Lysenko
authors.forename: Heong-Sub
authors.initials: HS
authors.lastname: Oh
authors.forename: Jin Kun
authors.initials: JK
authors.lastname: Cha
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D003516:Cycloparaffins / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000080:Acetals; D000447:Aldehydes; D003516:Cycloparaffins; D004987:Ethers; D004988:Ethers, Cyclic; D013141:Spiro Compounds; D014297:Trimethylsilyl Compounds; C043657:cyclopropanol