Stereoselective Synthesis of 3-Aminoindan-1-ones and Subsequent Incorporation into HIV-1 Protease Inhibitors
2006 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, no 3, 1265-1268 p.Article in journal (Refereed) Published
A new method for the stereoselective synthesis of 3-aminoindan-1-ones from triflates of salicylic sulfinyl imines and ethylene glycol vinyl ether has been developed. The reaction sequence starts with a regioselective Heck reaction followed by stereoselective Lewis acid mediated annulation. Acidic cleavage of the sulfinamides produced pure (R)- and (S)-3-aminoindan-1-ones, which were successfully isolated and incorporated into active HIV-1 protease inhibitors.
Place, publisher, year, edition, pages
2006. Vol. 71, no 3, 1265-1268 p.
HIV Protease Inhibitors/*chemical synthesis/chemistry/*pharmacology, Imines/chemistry, Indans/chemical synthesis/*chemistry/*pharmacology, Molecular Structure, Stereoisomerism, Sulfones/chemistry
Medical and Health Sciences
IdentifiersURN: urn:nbn:se:uu:diva-93600PubMedID: 16438552OAI: oai:DiVA.org:uu-93600DiVA: diva2:167127