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

共 35 条

[11] Catalytic asymmetric synthesis of chiral phosphanes [J].

Glueck, David S. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (24) :7108-7117

[12] Metal-catalyzed asymmetric synthesis of P-stereogenic Phosphines [J].

Glueck, David S. .

SYNLETT, 2007, (17) :2627-2634

[13] An air-stable, primary alkylphosphine: FcCH(2)PH(2) [Fc=(eta(5)-C5H5)Fe(eta(5)-C5H4)] [J].

Goodwin, NJ ;

Henderson, W ;

Nicholson, BK .

CHEMICAL COMMUNICATIONS, 1997, (01) :31-32

[14]

HERBERT JM, 1987, HETEROCYCLES, V26, P1037

[15] 1,8-DIFUNCTIONALIZED NAPHTHALENES AS BUILDING-BLOCKS - CONVENIENT LOW-TEMPERATURE SYNTHESIS OF 1-SILAACENAPHTHENES [J].

KIELY, JS ;

BOUDJOUK, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 182 (02) :173-183

[16] Alkylation of phosphine boranes by phase-transfer catalysis [J].

Lebel, H ;

Morin, S ;

Paquet, V .

ORGANIC LETTERS, 2003, 5 (13) :2347-2349

[17] Structural and electronic properties of heterofullerene C59P [J].

Lu, J ;

Zhou, YS ;

Luo, Y ;

Huang, YH ;

Zhang, XW ;

Zhao, XG .

MOLECULAR PHYSICS, 2001, 99 (14) :1203-1207

[18] AN EFFICIENT PROCEDURE FOR THE SYNTHESIS OF ELECTRON-RICH BISPHOSPHINES CONTAINING HOMOCHIRAL BACKBONES [J].

MCKINSTRY, L ;

LIVINGHOUSE, T .

TETRAHEDRON LETTERS, 1994, 35 (50) :9319-9322

[19]

Mezheritskii V.V., 1990, ADV HETEROCYCL CHEM, V51, P1, DOI [DOI 10.1016/50065-2725(08)60001-X, 10.1016/50065-2725(08)60001-X]

[20] Synthesis and molecular structures of dinuclear complexes with 1,2-dihydro-1,2-diphenyl-naphtho[1,8-c,d]1,2-diphosphole as a bridging ligand [J].

Mizuta, T ;

Kunikata, S ;

Miyoshi, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (16) :2624-2632

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