title: Monoprotection of diols as a key step for the selective synthesis of unequally disubstituted diamondoids (nanodiamonds).
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 S(N)1 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.
authors.affiliation: Institut für Organische Chemie, Justus-Liebig-Universität, Heinrich-Buff-Ring 58, 35392 Giessen, Germany.
authors.forename: Hartmut
authors.initials: H
authors.lastname: Schwertfeger
authors.forename: Christian
authors.initials: C
authors.lastname: Würtele
authors.forename: Michael
authors.initials: M
authors.lastname: Serafin
authors.forename: Heike
authors.initials: H
authors.lastname: Hausmann
authors.forename: Robert M K
authors.initials: RM
authors.lastname: Carlson
authors.forename: Jeremy E P
authors.initials: JE
authors.lastname: Dahl
authors.forename: Peter R
authors.initials: PR
authors.lastname: Schreiner