Metallocene sulfoxides as precursors of metallocenes with planar chirality

被引：75

作者：

Ferber, Benoit ^{[1
]}

Kagan, Henri B. ^{[1
]}

机构：

[1] Univ Paris 11, ICMMO, CNRS, UMR 8182, F-914055 Orsay, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 4-5期

关键词：

chiral ligands; enantioselective catalysis; ferrocenes; lithiation; planar chirality; sulfoxides;

D O I：

10.1002/adsc.200600639

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The preparation of metallocene sulfoxides and their ortho-diastereoselective functionalization are described. The applications of enantiopure 1,2- and 1,3-disubstituted metallocenes are reviewed, with special emphasis on the preparation of ligands for asymmetric catalysis. The sulfoxide functionality is a useful, traceless, chiral diastereoselective ortho-directing group, as explained in the article. It allows one to synthesize a wide range of enantiopure metallocenes with planar chirality and predictible configuration. Most of the examples are related to the ferrocene area.

引用

页码：493 / 507

页数：15

共 80 条

[21] REGIOSELECTIVE ORTHO SUBSTITUTION OF DIPHENYL SULFOXIDE CHROMIUM TRICARBONYL - COMPLEMENTARY STEREOSELECTIVITIES FOR THE MONO-ANIONS AND DI-ANIONS [J].

DAVIES, SG ;

LOVERIDGE, T ;

CLOUGH, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) :817-818

[22] HIGHLY ENANTIOSELECTIVE OXIDATION OF FERROCENYL SULFIDES [J].

DITER, P ;

SAMUEL, O ;

TAUDIEN, S ;

KAGAN, HB .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :549-552

[23] CARBON-SULFUR BOND-CLEAVAGE IN REACTION OF ALKYLLITHIUMS WITH SULFOXIDES [J].

DURST, T ;

LEBELLE, MJ ;

VANDENEL.R ;

TIN, KC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (05) :761-766

[24] ASYMMETRIC-SYNTHESIS OF CHIRAL ORGANOSULFUR COMPOUNDS USING N-SULFINYLOXAZOLIDINONES [J].

EVANS, DA ;

FAUL, MM ;

COLOMBO, L ;

BISAHA, JJ ;

CLARDY, J ;

CHERRY, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :5977-5985

[25] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN [J].

EVANS, DA ;

KALDOR, SW ;

JONES, TK ;

CLARDY, J ;

STOUT, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7001-7031

[26] A new efficient route to chiral 1,3-disubstituted ferrocenes:: Application to the syntheses of (Rp)- and (Sp)-17α-[(3′-formylferrocenyl)ethynyl]estradiol [J].

Ferber, B ;

Top, S ;

Welter, R ;

Jaouen, G .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (07) :2081-2086

[27] Recent developments in the synthesis and utilization of chiral sulfoxides [J].

Fernández, I ;

Khiar, N .

CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705

[28] The isopropylsulfinyl group:: A useful chiral controller for the asymmetric aziridination of sulfinylimines and the organocatalytic allylation of hydrazones [J].

Fernández, I ;

Valdivia, V ;

Gori, B ;

Alcudia, F ;

Alvarez, E ;

Khiar, N .

ORGANIC LETTERS, 2005, 7 (07) :1307-1310

[29]

Gomez Arrayas R., 2006, ANGEW CHEM, V118, P7836

[30] Diastereoselective addition of enantiopure lithium tert-butylsulfinylferrocene to imines [J].

Grach, Guillaume ;

Sopkova-de Oliveira Santos, Jana ;

Lohier, Jean-Francois ;

Mojovic, Ljubica ;

Ple, Nelly ;

Turck, Alain ;

Reboul, Vincent ;

Metzner, Patrick .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26) :9572-9579

← 1 2 3 4 5 6 7 8 →