Platinum-Catalyzed Enantioselective Tandem Alkylation/Arylation of Primary Phosphines. Asymmetric Synthesis of P-Stereogenic 1-Phosphaacenaphthenes
Organic Letters2008Vol. 10(20), pp. 4425–4428
Citations Over TimeTop 10% of 2008 papers
B. J. Anderson, M.A. Guino-O, David S. Glueck, James A. Golen, Antonio G. DiPasquale, Louise M. Liable‐Sands, Arnold L. Rheingold
Abstract
Enantioselective tandem alkylation/arylation of primary phosphines with 1-bromo-8-chloromethylnaphthalene catalyzed by Pt(DuPhos) complexes gave P-stereogenic 1-phosphaacenaphthenes (AcePhos) in up to 74% ee. Diastereoselective formation of four P-C bonds in one pot with bis(primary) phosphines gave C2-symmetric diphosphines, including the o-phenylene derivative DuAcePhos, for which the rac isomer was formed with high enantioselectivity. These reactions, which appear to proceed via an unusual metal-mediated nucleophilic aromatic substitution pathway, yield a new class of heterocycles with potential applications in asymmetric catalysis.
Related Papers
- → Resolution/Deracemization of Chiral α-Amino Acids Using Resolving Reagents with Flexible Stereogenic Centers(2009)95 cited
- → Applications of Diphosphines in Radical Reactions(2019)16 cited
- → Dibenzylamine substituted cyclotetraphosphazenes: Synthesis, characterization and their stereogenic properties(2018)5 cited
- → Investigations of olefin hydrogenation catalysts. The major species present in solutions containing rhodium(I) complexes of chelating diphosphines(1977)26 cited
- → Chiral ferrocenyl diphosphines for asymmetric transfer hydrogenation of acetophenone(2005)20 cited