1025935-06-1Relevant articles and documents
Enantioselective Synthesis of Nelfinavir via Asymmetric Bromocyclization of Bisallylic Amide
Nagao, Yoshihiro,Hisanaga, Tatsunari,Utsumi, Takahiro,Egami, Hiromichi,Kawato, Yuji,Hamashima, Yoshitaka
, p. 7290 - 7295 (2018)
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.