Synthesis of arylzinc thiolates containing perfluoroalkyl chains. Model catalyst precursors for the enantioselective zinc-mediated 1,2-addition of dialkylzincs to aldehydes in fluorous biphase systems

被引：40

作者：

Kleijn, H ^{[1
]}

Rijnberg, E ^{[1
]}

Jastrzebski, JTBH ^{[1
]}

van Koten, G ^{[1
]}

机构：

[1] Univ Utrecht, Debye Inst, Dept Met Mediated Synth, NL-3584 CH Utrecht, Netherlands

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 06期

关键词：

D O I：

10.1021/ol9907320

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis of perfluoroalkyl-functionalized arene trimethylsilyl others and their conversion to ethylzinc thiolates is described. These compounds have been successfully applied as catalysts in the enantioselective addition of diethylzinc to benzaldehyde. This is the first example of a two phase organic/perfluorous enantioselective catalytic system.

引用

页码：853 / 855

页数：3

共 11 条

[1] Fluorous phase separation techniques in catalysis [J].

de Wolf, E ;

van Koten, G ;

Deelman, BJ .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) :37-41

[2] WATER-SOLUBLE LIGANDS, METAL-COMPLEXES, AND CATALYSTS - SYNERGISM OF HOMOGENEOUS AND HETEROGENEOUS CATALYSIS [J].

HERRMANN, WA ;

KOHLPAINTNER, CW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (11) :1524-1544

[3] SULFUR DERIVATIVES OF EPHEDRA ALKALOIDS - NEW AND HIGHLY EFFICIENT CHIRAL CATALYSTS [J].

HOF, RP ;

POELERT, MA ;

PEPER, NCMW ;

KELLOGG, RM .

TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :31-34

[4] FACILE CATALYST SEPARATION WITHOUT WATER - FLUOROUS BIPHASE HYDROFORMYLATION OF OLEFINS [J].

HORVATH, IT ;

RABAI, J .

SCIENCE, 1994, 266 (5182) :72-75

[5]

JONES FN, 1963, J ORG CHEM, V28, P3461, DOI 10.1021/jo01047a045

[6] Ortho-bis(amino)arylnickel(II) halide complexes containing perfluoroalkyl chains as model catalyst precursors for use in fluorous biphase systems. [J].

Kleijn, H ;

Jastrzebski, JTBH ;

Gossage, RA ;

Kooijman, H ;

Spek, AL ;

van Koten, G .

TETRAHEDRON, 1998, 54 (07) :1145-1152

[7] SYNTHESIS AND PROPERTIES OF TRIMERIC ORTHO-CHELATED (ARENETHIOLATO)COPPER(I) COMPLEXES [J].

KNOTTER, DM ;

VANMAANEN, HL ;

GROVE, DM ;

SPEK, AL ;

VANKOTEN, G .

INORGANIC CHEMISTRY, 1991, 30 (17) :3309-3317

[8] Application of S,N-chelating chiral zinc bis(aminoarenethiolates) as new precursor catalysts in the enantioselective addition of dialkylzincs to aldehydes [J].

Rijnberg, E ;

Hovestad, NJ ;

Kleij, AW ;

Jastrzebski, JTBH ;

Boersma, J ;

Janssen, MD ;

Spek, AL ;

vanKoten, G .

ORGANOMETALLICS, 1997, 16 (13) :2847-2857

[9] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

SOAI, K ;

NIWA, S .

CHEMICAL REVIEWS, 1992, 92 (05) :833-856

[10]

Vries T, 1998, ANGEW CHEM INT EDIT, V37, P2349, DOI 10.1002/(SICI)1521-3773(19980918)37:17<2349::AID-ANIE2349>3.0.CO

← 1 2 →