title: Triflic Acid Promoted Decarboxylation of Adamantane-oxazolidine-2-one: Access to Chiral Amines and Heterocycles.
abstract: We have developed a one-step procedure to a variety of chiral lipophilic and conformationally rigid amines and heterocycles by decarboxylation of adamantane-oxazolidine-2-one. Triflic acid or aluminum triflate promote the addition of diverse nucleophiles to the oxazolidine-2-one moiety accompanied by the release of carbon dioxide. The resulting amine or heterocycle is then protonated/metalated by the catalyst (promotor). Additionally, the starting racemic material, adamantane-oxazolidine-2-one, was resolved into single enantiomers using a chiral auxiliary to access enantio-enriched products and to study the racemization pathway of chiral 1,2-disubstituted adamantane derivatives.
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University , Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
authors.forename: Radim
authors.identifier: 0000-0001-5060-6666
authors.initials: R
authors.lastname: Hrdina
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University , Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
authors.forename: Marta
authors.initials: M
authors.lastname: Larrosa
authors.affiliation: Institute of Inorganic and Analytical Chemistry, Justus-Liebig University , Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Logemann