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Org Lett. 2006 Nov 23;8(24):5661-4.

A general method for the catalytic nazarov cyclization of heteroaromatic compounds.

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1
Department of Chemistry, University of Rochester, Rochester, New York, 14627, USA.

Abstract

A general, catalytic method for efficient Nazarov cyclization of systems containing heteroaromatic components has been developed. Scandium triflate was identified as the most reactive promoter, and it was found that addition of lithium perchlorate was necessary for synthetically useful catalytic cyclizations. The method was used to synthesize a range of cyclopentanone-fused heteroaromatic systems in 36-97% yield, and the reactivity trends observed demonstrate the impact of polarization on cyclization efficiency. [reaction: see text].

PMID:
17107097
DOI:
10.1021/ol062403v
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