"Monoprotection of Diols as a Key Step for the Selective Synthesis of Unequally Disubstituted Diamondoids (Nanodiamonds)"

Hartmut Schwertfeger: Christian Würtele, Michael Serafin, Heike Hausmann, Robert M. K. Carlson, Jeremy E. P. Dahl and Peter R. Schreiner; J. Org. Chem., 08/29/08.

Additional Authors: Christian Würtele, Michael Serafin, Heike Hausmann, Robert M. K. Carlson, Jeremy E. P. Dahl and Peter R. Schreiner

Abstract:

The monoprotection (desymmetrization) of diamondoid, benzylic, and ethynyl diols has been achieved using fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) under acidic conditions. This practical acid-catalyzed SN1 reaction opens the door for the synthesis of novel bifunctional diamondoids. With diamantane as an example, we show that the resulting monoethers can be used to prepare selectively, for instance, amino or nitro alcohols and unnatural amino acids. These are important compounds in terms of the exploration of electronic, pharmacological, and material properties of functionalized nanodiamonds.