Platinum-Catalyzed Enantioselective Tandem Alkylation/Arylation of Primary Phosphines. Asymmetric Synthesis of P-Stereogenic 1-Phosphaacenaphthenes

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...

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Bibliographic Details
Published in:Organic letters 2008-10, Vol.10 (20), p.4425-4428
Main Authors: Anderson, Brian J, Guino-o, Marites A, Glueck, David S, Golen, James A, DiPasquale, Antonio G, Liable-Sands, Louise M, Rheingold, Arnold L
Format: Article
Language:English
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Summary: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 C 2-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801616s