Diastereoselective Prins-type reaction of cycloalkenylcyclopropanol silyl ethers and alpha,beta-unsaturated aldehyde acetals.
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.
Lysenko
Ivan L
IL
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
Oh
Heong-Sub
HS
Cha
Jin Kun
JK
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*
D000080:Acetals; D000447:Aldehydes; D003516:Cycloparaffins; D004987:Ethers; D004988:Ethers, Cyclic; D013141:Spiro Compounds; D014297:Trimethylsilyl Compounds; C043657:cyclopropanol