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

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

Organic letters (2007-02-08)
Tomoya Miura, Tatsuro Harumashi, Masahiro Murakami
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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Sigma-Aldrich
Methoxy(cyclooctadiene)rhodium(I) dimer