Novel ferrocenyl ligands with planar and central chirality in Pd-catalyzed allylic substitutions

被引：58

作者：

Enders, D ^{[1
]}

Peters, R ^{[1
]}

Runsink, J ^{[1
]}

Bats, JW ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 11期

关键词：

D O I：

10.1021/ol991139l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The use of planar chiral ferrocenyl ligands bearing a stereogenic center in beta-position of the side chain was investigated in Pd-catalyzed enantioselective allylic substitutions. By employing 2.2 mol % of a P,S-ligand and 1.0 mol % of [Pd(eta(3)-C3H5)Cl](2), the alkylation of the standard test system (+/-) (E)-diphenyl-2-propenyl acetate using dimethylmalonate/BSA as nucleophile proceeded in quantitative yield with an ee of 97%, which is the best value reported so far in this reaction using a P,S-ligand.

引用

页码：1863 / 1866

页数：4

共 25 条

[11]

Enders D., 1999, ANGEW CHEM, V111, P2579

[12]

HAYASHI T, 1993, CATALYTIC ASYMMETRIC, P325

[13] PALLADIUM PI-ALLYL CHEMISTRY OF NEW P,S BIDENTATE LIGANDS - SELECTIVE BUT VARIABLE DYNAMICS IN THE ISOMERIZATION OF THE ETA(3)-C3H5 AND ETA(3)-PHCHCHCHPH PI-ALLYL LIGANDS [J].

HERRMANN, J ;

PREGOSIN, PS ;

SALZMANN, R ;

ALBINATI, A .

ORGANOMETALLICS, 1995, 14 (07) :3311-3318

[14]

HUTTON AT, 1987, COMPREHENSIVE COORDI, V5, P551

[15] Chiral nonracemic pyridine thiols and thioethers applied in palladium-catalyzed allylic substitution. An example of near-perfect enantioselection [J].

Koning, B ;

Meetsma, A ;

Kellogg, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5533-5540

[16] C2-symmetric bisphosphinobioxazoline as a chiral ligand.: Highly enantioselective palladium-catalyzed allylic substitutions and formation of P,N,N,P tetradentate palladium (II) complexes [J].

Lee, S ;

Lim, CW ;

Song, CE ;

Kim, KM ;

Jun, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4445-4451

[17]

Muller A., 1987, COMPREHENSIVE COORDI, V2, P551

[18] Recent advances in the generation of non-racemic ferrocene derivatives and their application to asymmetric synthesis [J].

Richards, CJ ;

Locke, AJ .

TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2377-2407

[19] PHOSPHINOARYLOXAZOLINES AND PHOSPHINOALKYLOXAZOLINES AS NEW CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS - VERY HIGH ENANTIOSELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTIONS [J].

SPRINZ, J ;

HELMCHEN, G .

TETRAHEDRON LETTERS, 1993, 34 (11) :1769-1772

[20] Palladium-catalyzed asymmetric allylic amination using ferrocenyl pyrazole ligands: Steric control of eta(3)-allyl configuration and site-selective nucleophilic attack [J].

Togni, A ;

Burckhardt, U ;

Gramlich, V ;

Pregosin, PS ;

Salzmann, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1031-1037

← 1 2 3 →