Diastereoselective Prins-Type Reaction of Cycloalkenylcyclopropanol Silyl Ethers and α,β-Unsaturated Aldehyde Acetals

• Published in: Journal of organic chemistry Vol. 72; no. 21; pp. 7903 - 7908
• Main Authors: Lysenko, Ivan L, Oh, Heong-Sub, Cha, Jin Kun
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.10.2007; Amer Chemical Soc
• Subjects: Acetals - chemistry; Aldehydes - chemistry; Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Cycloparaffins - chemistry; Ethers - chemistry; Ethers, Cyclic - chemistry; Exact sciences and technology; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Stereoisomerism; Trimethylsilyl Compounds - chemistry; RADICAL RING EXPANSION; MODULAR APPROACH; VINYLCYCLOPROPANOLS; CONDENSATION; CYCLOPROPANES; FRAGMENTATION; ENANTIOSELECTIVE CONSTRUCTION; DERIVATIVES; CYCLOBUTANONES; CYCLIZATION; Unsaturated compound; Acetal; Enantioselectivity; Ether; Electrophilic addition; Organic siloxane; Organic silane; Aldehyde; Chemical synthesis; Acid medium; Prins reaction; Diastereoselectivity
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo071272o

Electrophilic addition of 1-(1-cyclohexenyl)-1-cyclopropanol trimethylsilyl ether to α,β-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 C 2-symmetric acetal. Elaboration of the resulting adducts provides ready access to medium-sized carbocycles.