Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides

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.

Graphical abstractIndium-mediated allylation of aldehydes, ketones, and sulfonimines with 2-(alkoxy)allyl bromides furnishes the corresponding homoallylic alcohols and sulfonamines in high yields. The products can be readily 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 products in moderate diastereomeric excess.Download full-size image