AI Article Synopsis
- A new one-step method was developed for creating chiral lipophilic and rigid amines by decarboxylating adamantane-oxazolidine-2-one.
- Triflic acid or aluminum triflate helps facilitate the reaction by promoting nucleophiles' addition while releasing carbon dioxide.
- The starting racemic adamantane-oxazolidine-2-one can be separated into single enantiomers using a chiral auxiliary to produce enantio-enriched products and examine the racemization process of these chiral derivatives.
Article 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.
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| http://dx.doi.org/10.1021/acs.joc.7b00711 | DOI Listing |
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