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Intramolecular iron-mediated diene/olefin cyclocoupling: formation of carbon spirocycles.

Organic letters (2004-07-17)
Anthony J Pearson, Xiaolong Wang, Ismet B Dorange
RÉSUMÉ

[reaction: see text] A short and convenient diastereoselective synthesis of all-carbon spirocylic molecules was developed. A straightforward protocol that involves rearrangement of the diene-Fe(CO)(3) complex followed by cyclization delivers the desired product. The reaction substrates were easily prepared by reaction of an appropriate nucleophile and a cyclohexadienyl-Fe(CO)(3) cation.

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(+)-Cedrol, ≥99.0% (sum of enantiomers, GC)