Organometallic compounds in organic synthesis—XI

Tricarbonyl[2–5-η-(methyl 3,5-dimethoxy-1α-methyl-2,4-cyclohexadiene-1β-carboxylate)]iron(0)

“…Substituent directive effects in the reactions of substituted cyclohexadienes with iron carbonyls have been studied extensively in these laboratories, by A. J. Birch and co-workers, with a view to exploiting the complexes so formed in organic synthesis (Birch et al, 1981;. The title complex results from reaction of the 2,5-diene (1) with Fe(CO)5 to yield both the a and fl isomers (2 and 3) in equal amounts .…”

New chemical and stereochemical applications of organoiron complexes

“…A few 1,3-diene tricarbonyliron complexes have been resolved, almost all by classical means (formation of diastereoisomeric derivatives) [ 449 , 457 , 487 – 490 ]. The first example of an enzymatic resolution of an organometallic complex has recently been reported [ 491 ].…”

“…The stereochemical synthesis exercised by a complexed transition-metal atom can often mimic the control exercised by enzymes but with a wider range of reaction mechanisms of substrates [ 445 , 456 ]. As compared to the classical synthesis approach, a new concept of superimposed lateral control of reactivity, stereochemistry and structure, by attachment of complexed metal ions to alkene and diene systems, has been discussed at length [ 457 ].…”

Synthesis and photophysical properties of iron-carbonyl complex–coumarin conjugates as potential bimodal IR–fluorescent probes

“…17 Numerous synthetic methods are currently available for the reaction of highly electrophilic tricarbonyliron cations with different types of nucleophiles. 15,18 Additionally, these procedures have been used, for example, to prepare iron-carbonyl flavonoid derivatives for an IR-based study of nod gene regulation in Rhizobium leguminosarum, 19 and most of these methods should clearly be suitable for the introduction of charged tricarbonyliron cation into the heteroaryl moiety, and they should be easily transferable to more sensitive 7-amino and 7-hydroxycoumarin derivatives, scaffolds that possess good fluorescence properties, and a marked fluorogenic character when their aniline or phenol is substituted with an electron-withdrawing group (EWG) used for designing pro-fluorophores suitable for "turn-on" fluorescent detection of various (bio)analytes.…”