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

Carbon−Carbon Bond-Forming Solid-Phase Reactions. Part II

“…Dolle and co-workers also reacted pinacol allyl boronate with polymer-bound aldehydes and found that allylindiums were also successfully condensed with these same aldehydes (Scheme 97). 117 The polymer-supported aldehydes could be aromatic The condensation of a dithiane anion with an aldehyde was demonstrated in the solid-phase synthesis of a dithiane-protected benzoin photolabile linker. 118 (5 examples 0-45% yield) or 99.5 (14 examples 0-80% yield).…”

“…Dolle and co-workers also reacted pinacol allyl boronate with polymer-bound aldehydes and found that allylindiums were also successfully condensed with these same aldehydes (Scheme ) . The polymer-supported aldehydes could be aromatic 97.1 or aliphatic 97.2 .…”

Indium in Organic Synthesis

“…The mild reaction conditions allowed for the use of base-labile linkers that would not be suitable with other metals used in this reaction. 48…”

Skeletal Diversity via a Branched Pathway: Efficient Synthesis of 29 400 Discrete, Polycyclic Compounds and Their Arraying into Stock Solutions

“…In separate reaction vessels, 64 hydroxyaldehydes were loaded onto macrobeads through silylation of their hydroxyl groups with the previously described macrobead-alkylsilyl triflate (illustrated with the silylation-loading of vanillin 1 in Figure ) . Each macrobead-loaded aldehyde was separately reacted with indium dust and 5-bromo-1,3-pentadiene in DMF, which provided the γ-addition product ( 2 in the illustrated case with vanillin) . Mesylation followed by elimination using DBU furnished the cross-conjugated triene (cf., 3 ) .…”