Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Organocatalytic Stereoconvergent Synthesis of α-CF3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis

Organocatalytic Stereoconvergent Synthesis of α-CF3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis
Darren Stead, Eva N. Lenz, Nigel S. Simpkins, Robert W. Foster
The highly enantioselective alkylation of α-CF3 enolates, generated from triketopiperazines, has been accomplished through use of a bifunctional thiourea organocatalyst to facilitate 1,4-addition to varied enone acceptors. On treatment with appropriate nitrogen nucleophiles, the chiral triketopiperazine products undergo a metamorphosis, to provide novel fused heterocyclic lactams such as extended pyrazolopyrimidines. All about that base: The organocatalytic stereoconvergent synthesis of α-CF3 amides has been developed. This approach has been used to access a diverse range of enantioenriched triketopiperazine products and a novel reaction mechanism has been elucidated. In addition, an enamine-mediated rearrangement was developed for the regioselective synthesis of enantiopure semi-saturated pyrazolopyrimidines.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701548

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