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

被引：69

作者：

Anderson, Brian J. ^{[1
]}

Guino-O, Marites A. ^{[1
]}

Glueck, David S. ^{[1
]}

Golen, James A. ^{[2
]}

DiPasquale, Antonio G. ^{[2
]}

Liable-Sands, Louise M. ^{[2
,3
]}

Rheingold, Arnold L. ^{[2
]}

机构：

[1] Dartmouth Coll, Dept Chem, Burke Lab 6128, Hanover, NH 03755 USA

[2] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA

[3] Widener Univ, Dept Chem, Chester, PA 19013 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 20期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ol801616s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective tandem alkylation/arylation of primary phosphines with 1-bromo-8-chloromethyl naphthalene 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.

引用

页码：4425 / 4428

页数：4

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