Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes

被引：87

作者：

Cabrera, S ^{[1
]}

Arrayás, RG ^{[1
]}

Carretero, JC ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 30期

关键词：

alkenes; asymmetric catalysis; ferrocenyl ligands; phenylsilyl; palladium; S ligands;

D O I：

10.1002/anie.200460087

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Open plan: Cationic methylpalladium(II) complexes of planar chiral Fesulphos ligands (Fesulphos = 1-phosphanyl-2-sulfenylferrocene) show excellent performance in the alkylative ring opening of oxa- and azabicyclic alkenes with dialkyl zinc reagents (see scheme, Cy = cyclohexyl, ArF = 3,5-bis (trifluoromethyl)phenyl). Catalyst loadings as low as 0.5 mol% are normally sufficient to achieve high enantioselectivities (94- > 99% ee).

引用

页码：3944 / 3947

页数：4

共 22 条

[1]

[Anonymous], ANGEW CHEM

[2] POLYMERS WITH MAIN-CHAIN CHIRALITY - SYNTHESIS OF HIGHLY ISOTACTIC, OPTICALLY-ACTIVE POLY(4-TERT-BUTYLSTYRENE-ALT-CO) USING PD(II) CATALYSTS BASED ON C-2-SYMMETRICAL BISOXAZOLINE LIGANDS [J].

BROOKHART, M ;

WAGNER, MI ;

BALAVOINE, GGA ;

HADDOU, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3641-3642

[3] Phosphinidine-palladium complexes for the polymerization and oligomerization of ethylene [J].

Daugulis, O ;

Brookhart, M ;

White, PS .

ORGANOMETALLICS, 2002, 21 (26) :5935-5943

[4]

Enders D, 2000, EUR J ORG CHEM, V2000, P3399

[5] Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes [J].

Evans, DA ;

Michael, FE ;

Tedrow, JS ;

Campos, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3534-3543

[6] Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions [J].

Evans, DA ;

Campos, KR ;

Tedrow, JS ;

Michael, FE ;

Gagné, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7905-7920

[7] MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST [J].

HUBERT, AJ .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :1984-&

[8] Enantio- and diastereoselective Ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives [J].

Kanayama, T ;

Yoshida, K ;

Miyabe, H ;

Takemoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2054-2056

[9] Mechanistic studies of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc [J].

Lautens, M ;

Hiebert, S ;

Renaud, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6834-6839

[10] Enantioselective ring opening of aza and oxabicyclic alkenes with dimethylzinc [J].

Lautens, M ;

Hiebert, S ;

Renaud, JL .

ORGANIC LETTERS, 2000, 2 (13) :1971-1973

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