Intramolecular reactions of hydroperoxides and oxetanes: stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes.
[reactions: see text] The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.
Dai
Peng
P
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.
Dussault
Patrick H
PH
D000080:Acetals / Q000737:chemistry; D000478:Alkylation; D001688:Biological Products / Q000737:chemistry; D003500:Cyclization; D004146:Dioxanes / Q000138:chemical synthesis / Q000737:chemistry*; D004148:Dioxolanes / Q000138:chemical synthesis / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000080:Acetals; D001688:Biological Products; D004146:Dioxanes; D004148:Dioxolanes; D004988:Ethers, Cyclic; D006861:Hydrogen Peroxide; C005287:oxetane