Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 23; pp. 3831 - 3843
• Main Authors: Donaldson, William A., Chaudhury, Subhabrata
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2009; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemical reactivity; Chemistry; Coordination compounds; Diene ligands; Exact sciences and technology; Inorganic chemistry and origins of life; Iron; Nucleophilic addition; Organic chemistry; Preparations and properties; Reactivity and mechanisms; Regioselectivity; Synthetic methods; Transition element complexes; Cyclopropane derivatives; Ligand; Iron; Unsaturated compound; Steric effect; Carbocation; Synthetic methods; Chemical reactivity; Chemical synthesis; Protection; Complexation; Oxidation reduction; Regioselectivity; Steric hindrance; Transition metal Carbonyl Complexes; Transition metal; Transition metal Complexes; Natural compound; Dienic compound; Cycloaddition; Iron Carbonyl Complexes; Iron complex; Polyenic compound; Analog; Cations; Diene ligands; Nucleophilic addition
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200900141

Complexation of (tricarbonyl)iron to an acyclic diene serves to protect the ligand against oxidation, reduction, and cycloaddition reactions, whereas the steric bulk of this adjunct serves to direct the approaches of reagents to unsaturated groups attached to the diene onto the face opposite to iron. Furthermore, the Fe(CO)3 moiety can serve to stabilize carbocation centers adjacent to the diene (i.e. pentadienyl‐iron cations). Recent applications of these reactivities to the synthesis of polyene‐, cyclopropane‐, cycloheptadiene‐, and cyclohexenone‐containing natural products or analogues are presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Recent applications of organoiron complexes to the synthesis of conjugated polyenes, cyclopropanes, and cycloheptadienes are reviewed.