Enantioselective Synthesis of Nelfinavir via Asymmetric Bromocyclization of Bisallylic Amide

The Journal of Organic Chemistry
Yoshihiro NagaoYoshitaka Hamashima

Abstract

We describe a concise enantioselective synthesis of the HIV-protease inhibitor nelfinavir (1) via a new route in which the key step is construction of the central optically active 1,2-amino alcohol framework via asymmetric bromocyclization of bisallylic amide with N-bromosuccinimide in the presence of a catalytic amount of ( S)-BINAP or ( S)-BINAP monoxide. The remaining alkene and bromo functionalities were used to install the requisite thioether and chiral perhydroisoquinoline units, respectively.

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