title: Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes.
abstract: An efficient TiCl(4)-Et(3)N or Bu(3)N-promoted aldol-type addition of phenyl and thiophenyl esters or thioaryl esters with aldehydes and ketones was performed (total 46 examples). The present method is advantageous from atom-economical and cost-effective viewpoints; good to excellent yields, moderate to good syn-selectivity, substrate variations, reagent availability, and simple procedures. Utilizing the present reaction as the key step, an efficient short synthesis of three lactone [2(5H)-furanone] analogs of jasmine perfumes was performed. Among them, the lactone analog of cis-jasmone had a unique perfume property (tabac).
authors.affiliation: Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
authors.forename: Ryohei
authors.initials: R
authors.lastname: Nagase
authors.forename: Noriaki
authors.initials: N
authors.lastname: Matsumoto
authors.forename: Kohei
authors.initials: K
authors.lastname: Hosomi
authors.forename: Takahiro
authors.initials: T
authors.lastname: Higashi
authors.forename: Syunsuke
authors.initials: S
authors.lastname: Funakoshi
authors.forename: Tomonori
authors.initials: T
authors.lastname: Misaki
authors.forename: Yoo
authors.initials: Y
authors.lastname: Tanabe