We have demonstrated that 1,3-disiloxanediols are active hydrogen-bonding and anion-binding catalysts. This presentation will discuss improved methods for the synthesis of various 1,3-disiloxanediols and efforts for the synthesis of chiral 1,3-disiloxanediols. An organocatalytic method has been applied for the direct hydrolysis of 1,3-dihydrodisiloxanes to their corresponding disiloxanediols in good yield.  A comparison of catalytic conditions for silane hydrolysis and mechanistic studies will be presented. The development of methods and conditions using a combination of chiral auxiliaries and asymmetric reactions will be described for the synthesis of enantioenriched chiral disiloxanediols.  <sup>1</sup>H NMR experiments are utilized to quantify hydrogen-bonding and anion-binding abilities of various 1,3-disiloxanediols relative for catalysis.  The catalytic activity of 1,3-disiloxanediols and new chiral variants will also be discussed.

Metal-free synthesis of 1,3-disiloxanediols and methods toward chiral variants for asymmetric catalysis

253rd National Meeting (2017)

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