Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 257-265
doi:10.1351/pac200678020257
Sulfenylphosphinoferrocenes: Novel planar chiral ligands in enantioselective catalysis*
Silvia Cabrera, Olga García Mancheño, Ramón Gómez Arrayás,Inés Alonso, Pablo Mauleón, and Juan C. Carretero
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain
Abstract:
Structurally well-defined transition-metal complexes of 1-phosphino-2-sulfenylferrocene (Fesulphos ligands) act as highly efficient catalysts in a variety of mechanistically different transformations. Excellent enantioselectivities were achieved in Pd-catalyzed allylic substitutions, desymmetrization of meso-heterobicyclic alkenes by Pd-catalyzed addition of dialkylzinc reagents, Pd-catalyzed Diels-Alder reaction of cyclopentadiene with N-acryloyl oxazolidinones, and in Cu-catalyzed formal aza-Diels-Alder reaction of Danishefsky diene to N-sulfonyl aldimines.
Keywords: allylic substitutions; Cu-catalyzed; Danishefsky diene; desymmetrization; enantioselective; Fesulphos; N-sulfonyl aldimines; Pd-catalyzed; sulfenylphosphinoferrocenes.
*Pure Appl. Chem. 78, 197-523. An issue of reviews and research papers based on lectures presented at the 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), Geneva, Switzerland, 17-21 July 2005.