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

Cullen L. Cavallaro, Timothy Herpin, Brian F. McGuinness, Yvonne Class Shimshock, Roland E. Dolle

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Homoallylic alcohols are prepared in high yield and puritY by the reaction of the title reagents with resin-bound aldehydes. The mild reaction conditions accommodate the base-sensitive 4-carboxamido-3-nitrobenzyl photolabile linker on standard resins. A practical application of the allylation reaction is demonstrated through the solid-phase synthesis of hydroxypropylamines.

Original languageEnglish
Pages (from-to)2711-2714
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number14
DOIs
StatePublished - Apr 2 1999

Keywords

  • Allylation
  • Homoallylic alcohol
  • Indium
  • Solid-phase synthesis, hydroxypropylamine

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