Organocatalytic Stereoconvergent Synthesis of [alpha]-CF3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis

The highly enantioselective alkylation of [alpha]-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 triketo...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-07, Vol.23 (37), p.8810
Main Authors: Foster, Robert W, Lenz, Eva N, Simpkins, Nigel S, Stead, Darren
Format: Article
Language:English
Subjects:
Alkylation
Amides
Chemistry
Enantiomers
Metamorphosis
Nitrogen
Nucleophiles
Pyrazolopyrimidines
Thiourea
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Summary:The highly enantioselective alkylation of [alpha]-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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201701548