Abstract
A diversity-oriented protocol giving access to a novel class
of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed,
three-component coupling of a ketone, an alkyne and a primary amine
(KA² -coupling) provides the required secondary
propargylamines and assures the generation of diversity. The key
step of the protocol, a silver(I)-mediated tandem guanylation of secondary
propargylamines followed by an intramolecular heterocyclization,
provides the target bis-Boc-protected-2-iminoimidazolines spiro-fused
with a five-, six- or seven-membered (heterocyclic) ring, which
could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.
Key words
2-aminoimidazoles - spiro compounds - tandem
reaction - ring closure - silver
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27 See Supporting Information for details.
28 CCDC-801762 contains the supplementary
crystallographic data for this paper and can be obtained free of
charge via www.ccdc.cam.ac.uk/conts/retrieving.html
(or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge
CB2 1EZ, UK; fax:+44(1223)336033; or deposit@ccdc.cam.ac.uk).
