Stereoselective Synthesis of 3-Aminoindan-1-ones and Subsequent Incorporation into HIV-1 Protease Inhibitors

• 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.

Nyckelord

HIV Protease Inhibitors/*chemical synthesis/chemistry/*pharmacology

Imines/chemistry

Indans/chemical synthesis/*chemistry/*pharmacology

Molecular Structure

Stereoisomerism

Sulfones/chemistry

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