Air-stable bifunctional allylation reagents for the asymmetric synthesis of differentiated syn- and anti-1,3-diols

Turning the diols: Enantiomerically pure bifunctional reagents I and ent-I undergo asymmetric aldehyde allylation followed by Ir(I)-catalyzed enantioselective decarboxylative allylic etherification to give differentiated syn- and anti-1,3-diols with complete control of the absolute and relative stereochemistry (see scheme; PMP = para-methoxyphenyl, dbcot = dibenzo[a,e]cyclooctatetraene, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).