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J Am Chem Soc. 2003 Nov 26;125(47):14278-9.

Polarizing the Nazarov cyclization: efficient catalysis under mild conditions.

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1
Department of Chemistry, University of Rochester, Rochester, NY 14627, USA.

Erratum in

  • J Am Chem Soc. 2004 Aug 25;126(33):10493.

Abstract

Substituted divinyl ketones were studied in the Nazarov cyclization. alpha-Carbomethoxy divinyl ketones underwent efficient Nazarov cyclization with catalytic copper triflate (2 mol %) to give a single cyclopentenone regio- and stereoisomer. The efficiency of the cyclizations correlated with the ability of the substituents to favorably polarize the pi-system of the cationic intermediate.

PMID:
14624567
DOI:
10.1021/ja037910b
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