Synthesis of Bicyclic Guanidines via Cascade Hydroamination/Michael Additions of Mono‑N‑acryloylpropargylguanidines

A cascade silver­(I)-catalyzed hydroamination/Michael addition sequence has been developed to deliver highly substituted bicyclic guanidines. This transformation gives rise to geometrically and constitutionally stable ene–guanidines and generates a remote stereocenter with moderate to high diastereo...

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Bibliographic Details
Published in:Organic letters 2014-12, Vol.16 (23), p.6048-6051
Main Authors: Kwon, Ki-Hyeok, Serrano, Catherine M, Koch, Michael, Barrows, Louis R, Looper, Ryan E
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Guanidines - chemical synthesis
Guanidines - chemistry
Letter
Molecular Structure
Silver - chemistry
Stereoisomerism
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Summary:A cascade silver­(I)-catalyzed hydroamination/Michael addition sequence has been developed to deliver highly substituted bicyclic guanidines. This transformation gives rise to geometrically and constitutionally stable ene–guanidines and generates a remote stereocenter with moderate to high diastereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502691w