Double cyclization via intramolecular coupling between cyclohexadiene-Fe(CO)3 complexes and pendant conjugated dienes

Anthony J Pearson; Xiaolong Wang

doi:10.1021/ja0210188

Double cyclization via intramolecular coupling between cyclohexadiene-Fe(CO)3 complexes and pendant conjugated dienes

J Am Chem Soc. 2003 Jan 22;125(3):638-9. doi: 10.1021/ja0210188.

Authors

Anthony J Pearson¹, Xiaolong Wang

Affiliation

¹ Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA. [email protected]

PMID: 12526656
DOI: 10.1021/ja0210188

Abstract

Intramolecular double cyclization between a cyclohexadiene-Fe(CO)3 complex and a pendant diene yielded a tricyclic molecule containing a spirocenter, with defined relative stereochemistry of four contiguous carbon centers. The nature of the substituent on the pendant diene moiety has a significant effect on the yield: an ester group leads to lower yield. The product has a conjugated cyclohexadiene or methoxycyclohexadiene system; the latter was converted to an enone.