Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines

Homoallylic alcohols are prepared in high yield and purity by the reaction of the title reagents with resin-bound aldehydes. The mild reaction conditi ons accommodate the base-sensitive 4-carboxamido-3-nitrobenzyl photolabile linker on standard resins. A practical application of the allylation reacti on is demonstrated through the solid-phase synthesis of hydroxypropylamines . (C) 1999 Elsevier Science Ltd. All rights reserved.