Journal article

Publication year: 2017

Pages: 4891-4899

Journal: The Journal of Organic Chemistry

Volume number: 82

Issue number: 9

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/acs.joc.7b00711

Publisher: American Chemical Society

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 enantioenriched products and to study the racemization pathway of chiral 1,2-disubstituted adamantane derivatives.

Harvard Citation style: Hrdina, R., Larrosa, M. and Logemann, C. (2017) Triflic Acid Promoted Decarboxylation of Adamantane-oxazolidine-2-one: Access to Chiral Amines and Heterocycles, The Journal of Organic Chemistry, 82(9), pp. 4891-4899. https://doi.org/10.1021/acs.joc.7b00711

APA Citation style: Hrdina, R., Larrosa, M., & Logemann, C. (2017). Triflic Acid Promoted Decarboxylation of Adamantane-oxazolidine-2-one: Access to Chiral Amines and Heterocycles. The Journal of Organic Chemistry. 82(9), 4891-4899. https://doi.org/10.1021/acs.joc.7b00711