Synthesis of [3]Ferrocenophanes via
Samarium Diiodide Promoted Reductive
Cyclizations of
1,1‘-Dicinnamoylferrocenes
Shean-Jeng Jong
Jim-Min Fang
10.1021/ol0060228.s001
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_3_Ferrocenophanes_via_Samarium_Diiodide_Promoted_Reductive_Cyclizations_of_1_1_-Dicinnamoylferrocenes/3736440
A series of 1,1‘-dicinnamoylferrocenes were converted to the corresponding [3]ferrocenophane diols (<b>4a</b>−<b>e</b>) 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 (<b>I</b><b><sub>A</sub></b>) having the moieties of<i> s</i>-<i>cis</i> enone and (<i>Z</i>)-enolate. A solid-state
structure of such [3]ferrocenophane diol product showed that the cyclopentadienyl groups were in an eclipsed orientation and slightly tilted.
2000-06-01 00:00:00
cyclopentadienyl groups
samarium diiodide
diol
stereoselective manner
aldol reaction
samarium chelated transition state
Samarium Diiodide Promoted Reductive Cyclizations
reaction pathway
ferrocenophane
cis enone