title: Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides.
abstract: 2-(Alkoxy)propenyl bromides are readily prepared from 1,3-dibromo-2-propanol in a two-step sequence involving hydroxyl protection and sodium hydride-induced dehydrobromination. Indium-mediated allylation of aldehydes, ketones, and sulfonimines with 2-(alkoxy)propenyl bromides furnishes the corresponding homoallylic alcohols and sulfonamines in good yields. The products can be easily transformed into β-hydroxy ketones and esters, as well as substituted dihydropyrans and protected β-amino acids. Chiral 2-(alkoxy)propenyl halides, derived from (-)-menthol and D-glucal, furnish diastereomerically enriched products.
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Northridge 18111 Nordhoff, Street, Northridge, CA 91330.
authors.forename: Heemal
authors.initials: H
authors.lastname: Dhanjee
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan