title: Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity.
abstract: The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave alpha-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of alpha-hydroxy chromanone in >90% ee was demonstrated using this method.
authors.affiliation: Department of Process Research, Merck and Co., P.O. Box 2000, Rahway, New Jersey 07765, USA. ben_marcune@merck.com
authors.forename: Benjamin F
authors.initials: BF
authors.lastname: Marcune
authors.forename: Sandor
authors.initials: S
authors.lastname: Karady
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Reider
authors.forename: Ross A
authors.initials: RA
authors.lastname: Miller
authors.forename: Mirlinda
authors.initials: M
authors.lastname: Biba
authors.forename: Lisa
authors.initials: L
authors.lastname: DiMichele
authors.forename: Robert A
authors.initials: RA
authors.lastname: Reamer