Opening of substituted oxetanes with H(2)O(2) and alkyl hydroperoxides: stereoselective approach to 3-peroxyalcohols and 1,2,4-trioxepanes.
[reaction: see text] Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.
Dussault
Patrick H
PH
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA. pdussault1@unl.edu
Trullinger
Tony K
TK
Noor-e-Ain
Farhana
F
D000962:Antimalarials / Q000138:chemical synthesis; D004148:Dioxolanes / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000962:Antimalarials; D004148:Dioxolanes; D004988:Ethers, Cyclic; D010545:Peroxides; C005287:oxetane