ol0060228_si_001.pdf (66.47 kB)
Synthesis of [3]Ferrocenophanes via Samarium Diiodide Promoted Reductive Cyclizations of 1,1‘-Dicinnamoylferrocenes
journal contribution
posted on 2000-06-01, 00:00 authored by Shean-Jeng Jong, Jim-Min FangA series of 1,1‘-dicinnamoylferrocenes were converted to the corresponding [3]ferrocenophane diols (4a−e) in a stereoselective manner by
using samarium diiodide to effect the intramolecular coupling reaction, aldol reaction, and reduction in one-pot operation. The major reaction
pathway might be derived from a samarium chelated transition state (IA) having the moieties of s-cis enone and (Z)-enolate. A solid-state
structure of such [3]ferrocenophane diol product showed that the cyclopentadienyl groups were in an eclipsed orientation and slightly tilted.