title: Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one.
abstract: A three-step synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one (1) from (R)-(+)-pulegone (3), proceeding in 44% overall yield, is described. The sequence comprises vinyl triflate formation, site-selective ozonolysis, and reduction. The route requires only one chromatographic purification and provides a convenient method to access multigram quantities of (R)-(+)-4-methylcyclohex-2-ene-1-one (1).
authors.affiliation: Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
authors.forename: Maung Kyaw Moe
authors.initials: MK
authors.lastname: Tun
authors.forename: Seth B
authors.initials: SB
authors.lastname: Herzon
mesh_terms: D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones; D039821:Monoterpenes; C039648:pulegone