Air-Stable Bifunctional Allylation Reagents for the Asymmetric Synthesis of Differentiated syn- and anti-1,3-Diols

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Abstract

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Turning the diols: Enantiomerically pure bifunctional reagents I and ent-I undergo asymmetric aldehyde allylation followed by IrI-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).

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