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Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S E ′ reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at −78°C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed...
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