Asymmetric intermolecular C-H activation, using immobilized dirhodium tetrakis((S)-N-(dodecylbenzenesulfonyl)-prolinate) as a recoverable catalyst

被引：69

作者：

Davies, HML ^{[1
]}

Walji, AM ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol0273506

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Heterogenization of dirhodium tetrakis((S)-N-dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be readily achieved on a pyridine functionalized highly cross-linked polystyrene resin. The immobilized complex is readily recycled and exhibits excellent catalytic activity for asymmetric intermolecular C-H activation by means of rhodium carbenoid induced C-H insertion.

引用

收藏

页码：479 / 482

页数：4

相关论文

共 28 条

[1]

ANNUNZIATA R, 2001, J ORG CHEM, V113, P2587

[2] Enantioselective synthesis of D-threo-methylphenidate [J].

Axten, JM ;

Ivy, R ;

Krim, L ;

Winkler, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) :6511-6512

[3]

Bergbreiter D.E., 2000, CHIRAL CATALYST IMMO, P43

[4] CATALYTIC CYCLOPROPANATION WITH TRANSITION-METAL SALTS OF SOLUBLE POLYETHYLENE CARBOXYLATES [J].

BERGBREITER, DE ;

MORVANT, M ;

CHEN, B .

TETRAHEDRON LETTERS, 1991, 32 (24) :2731-2734

[5] Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions [J].

Burguete, MI ;

Fraile, JM ;

García, JI ;

García-Verdugo, E ;

Herrerías, CI ;

Luis, SV ;

Mayoral, JA .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8893-8901

[6] Polymer-supported bis(oxazoline)-copper complexes as catalysts in cyclopropanation reactions [J].

Burguete, MI ;

Fraile, JM ;

García, JI ;

García-Verdugo, E ;

Luis, SV ;

Mayoral, JA .

ORGANIC LETTERS, 2000, 2 (24) :3905-3908

[7] The first immobilization of pyridine-bis(oxazoline) chiral ligands [J].

Cornejo, A ;

Fraile, JM ;

García, JI ;

García-Verdugo, E ;

Gil, MJ ;

Legarreta, G ;

Luis, SV ;

Martínez-Merino, V ;

Mayoral, JA .

ORGANIC LETTERS, 2002, 4 (22) :3927-3930

[8]

Davies H. M. L., 2001, ORG REACTIONS, V59, P1

[9] Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran [J].

Davies, HML ;

Hansen, T ;

Churchill, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3063-3070

[10] Catalytic asymmetric C-H activation of sp3 hybridized C-H bonds by means of carbenoid C-H insertions:: applications in organic synthesis [J].

Davies, HML .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 189 (01) :125-135