title: trans-2-Tritylcyclohexanol as a chiral auxiliary in permanganate-mediated oxidative cyclization of 2-methylenehept-5-enoates: application to the synthesis of trans-(+)-linalool oxide.
abstract: The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (dr ∼97:3). Chiral resolution of (±)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.
authors.affiliation: Department of Chemistry, The University of Southampton , Highfield, Southampton SO17 1BJ, U.K.
authors.forename: Ali M
authors.initials: AM
authors.lastname: Al Hazmi
authors.forename: Nadeem S
authors.initials: NS
authors.lastname: Sheikh
authors.forename: Carole J R
authors.initials: CJ
authors.lastname: Bataille
authors.forename: Azzam A M
authors.initials: AA
authors.lastname: Al-Hadedi
authors.forename: Sam V
authors.initials: SV
authors.lastname: Watkin
authors.forename: Tim J
authors.initials: TJ
authors.lastname: Luker
authors.forename: Nicholas P
authors.initials: NP
authors.lastname: Camp
authors.forename: Richard C D
authors.initials: RC
authors.lastname: Brown
mesh_terms: D000080462:Acyclic Monoterpenes; D003500:Cyclization; D003511:Cyclohexanols / Q000737:chemistry*; D017895:Manganese Compounds / Q000737:chemistry*; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
chemical_list: D000080462:Acyclic Monoterpenes; D003511:Cyclohexanols; D017895:Manganese Compounds; D039821:Monoterpenes; D010087:Oxides; D014320:Triphenylmethyl Compounds; C048856:permanganic acid; C000593345:linalool oxide; C018584:linalool