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Synthesis of bicyclic guanidines via cascade hydroamination/Michael additions of mono-N-acryloylpropargylguanidines.

ABSTRACT: 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.

SUBMITTER: Kwon KH

PROVIDER: S-EPMC4260634 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Synthesis of bicyclic guanidines via cascade hydroamination/Michael additions of mono-N-acryloylpropargylguanidines.

Kwon Ki-Hyeok KH Serrano Catherine M CM Koch Michael M Barrows Louis R LR Looper Ryan E RE

Organic letters 20141113 23

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. ...[more]

PMID: 25393831

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