Palladium complexes of chiral planar 1-phosphino-2-sulfenylferrocenes as efficient catalysts in enantioselective Diels-Alder reactions

被引：39

作者：

Mancheño, OG ^{[1
]}

Arrayás, RG ^{[1
]}

Carretero, JC ^{[1
]}

机构：

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

来源：

ORGANOMETALLICS | 2005年 / 24卷 / 04期

关键词：

D O I：

10.1021/om0493762

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The readily available dichloride palladium complexes of chiral planar (R)-1-phosphino-2-sulfenylferrocenes (Fesulphos ligands) act as efficient Lewis acids in the catalytic asymmetric Diels-Alder reaction of cyclopentadiene with acryloyl-1,3-oxazolidin-2-one. Very high enantioselectivities, up to 95% ee, have been reached from Fesulphos ligands having a very bulky substitution at both sulfur and phosphorus coordinating atoms.

引用

页码：557 / 561

页数：5

共 49 条

[31]

Kündig EP, 2001, ADV SYNTH CATAL, V343, P51

[32]

KUNDIG PE, 2000, LEWIS ACIDS ORGANIC, V2, P631

[33] Glyoxal bis-hydrazones:: a new family of nitrogen ligands for asymmetric catalysis [J].

Lassaletta, JM ;

Alcarazo, M ;

Fernández, R .

CHEMICAL COMMUNICATIONS, 2004, (03) :298-299

[34] Chiral copper complexes of phosphino sulfenyl ferrocenes as efficient catalysts for enantioselective formal Aza Diels-Alder reactions of N-sulfonyl Imines [J].

Mancheño, OG ;

Arrayás, RG ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :456-457

[35] 1-phosphino-2-sulfenylferrocenes as planar chiral ligands in enantioselective palladium-catalyzed allylic substitutions [J].

Mancheño, OG ;

Priego, J ;

Cabrera, S ;

Arrayás, RG ;

Llamas, T ;

Carretero, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3679-3686

[36] Chiral thioether ligands:: coordination chemistry and asymmetric catalysis [J].

Masdeu-Bultó, AM ;

Diéguez, M ;

Martin, E ;

Gómez, M .

COORDINATION CHEMISTRY REVIEWS, 2003, 242 (1-2) :159-201

[37] Novel chiral sulfur-containing ferrocenyl ligands for palladium-catalyzed asymmetric allylic substitution [J].

Nakamura, S ;

Fukuzumi, T ;

Toru, T .

CHIRALITY, 2004, 16 (01) :10-12

[38] Chiral phosphinooxathiane ligands for catalytic asymmetric Diels-Alder reaction [J].

Nakano, H ;

Suzuki, Y ;

Kabuto, C ;

Fujita, R ;

Hongo, H .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :5011-5014

[39] A novel and efficient chiral palladium-phosphinooxazolidine catalyst for the enantioselective Diels-Alder reaction [J].

Nakano, H ;

Okuyama, Y ;

Suzuki, Y ;

Fujita, R ;

Kabuto, C .

CHEMICAL COMMUNICATIONS, 2002, (10) :1146-1147

[40] A cationic palladium(II) complex-catalyzed Diels-Alder reaction [J].

Oi, S ;

Kashiwagi, K ;

Inoue, Y .

TETRAHEDRON LETTERS, 1998, 39 (34) :6253-6256

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