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Organic letters

Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons.


PMID 17284039

Abstract

[reaction: see text] Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered beta-enamino esters in good yield. An (oxa-pi-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

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661058
Methoxy(cyclooctadiene)rhodium(I) dimer
C18H30O2Rh2