Stabilised enamine anions. Generation and alkylation of anions stabilised as cyclopentadienide enamine systems

Acid-Promoted Iso-Nazarov Cyclization of Conjugated trans-Dienones and Dienals for the Synthesis of 2-Cyclopentenones

“…13 C­{ 1 H} NMR (CDCl 3 , 75 MHz) : δ 208.6 (C, C-1), 169.1 (C, C-3), 142.4 (C, C-1′′), 137.7 (C, C-2), 135.2 (C, C-1′), 128.9 (CH, C-4′), 128.7 (2 × CH, C-3′′), 128.3 (2 × CH, C-2′), 128.0 (2 × CH, C-3′), 127.3 (2 × CH, C-2′′), 126.7 (CH, C-4′′), 47.1 (CH, C-4), 45.1 (CH 2 , C-5), 9.9 (CH 3 , C2-CH 3 ). All of the spectral data matches those reported in the literature …”

“…Some reactions could be run both in toluene and 1,2-dichloroethane, in every case affording better results using the chlorinated solvent (see the SI for toluene results). In particular, product 14e , obtained in 40% yield using substrate 13e , is a commercial product and has been previously prepared by other methodologies which either involve many synthetic steps and/or the use of delicate reagents that require careful handling . Due to the interest in 14e and the ready availability of the corresponding substrate 13e , this cyclization reaction was then attempted on a gram scale (1 g of 13e ) without affecting the yield of product 14e (40%).…”

Aminoferrocenes and Aminocobaltocenes as Redox-Active Chelating Ligands: Syntheses, Structures, and Coordination Chemistry1

“…While the enamine reaction with sec-amines and 2-indanone is well established, up to our work only a single example of enamine formation from a cyclopentenone and an amine had been described …”

Molybdenum complexes containing substituted cyclopenta[l]phenanthrenyl ligand

“…Synthesis of amino-functionalized cyclopentadienes [23,24] and indenes [23][24][25][26] through reaction of the cyclopentenone (indanone) with secondary amines and their use for synthesis of the transition metal complexes [22][23][24][25][26] was the subject of several studies. However this is the first example of applying this method to the synthesis of the cyclopentadienyl-based framework containing both tertiary amino and carboxylic ester groups.…”