Catalytic-enantioselective methoxycarbonylation of 1,3-dichloroarene-tricarbonyl-chromium(0) complexes:: A desymmetrization approach to planar chirality

被引：26

作者：

Böttcher, A ^{[1
]}

Schmalz, HG ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

SYNLETT | 2003年 / 11期

关键词：

arene complexes; asymmetric catalysis; chromium; kinetic resolution; palladium;

D O I：

10.1055/s-2003-41417

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd-catalyzed mono-methoxycarbonylation of prochiral 1,3-dichloroarene-Cr(CO)(3) complexes was investigated. In the presence of the chiral ferrocene ligand (R,S-p)-PPF-pyrrolidine the planar-chiral products were obtained with up to 90% ee (53% yield). A strong dependence of the enantioselectivity on the reaction time was observed. A kinetic study using eta(6)- (2,6-dichlorotoluene)Cr(CO)(3) revealed that the initial enantiomeric purity of the monomethoxycarbonylated product is further enhanced due to a kinetic resolution (S = 4.3) connected to the formation of the bis-methoxy-carbonylated side-product.

引用

页码：1595 / 1598

页数：4

共 22 条

[1]

[Anonymous], 2000, J AM CHEM SOC, V122, P8083

[2] Planar chiral arene chromium(0) complexes:: potential ligands for asymmetric catalysis [J].

Bolm, C ;

Muñiz, K .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) :51-59

[3] Kinetic resolution of racemic tricarbonyl(2-chloroanisole)chromium via palladium-catalysed asymmetric alkoxycarbonylation [J].

Carpentier, JF ;

Pamart, L ;

Maciewjeski, L ;

Castanet, Y ;

Brocard, J ;

Mortreux, A .

TETRAHEDRON LETTERS, 1996, 37 (02) :167-170

[4] ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED BENZYL ALCOHOLS VIA THE STEREOSELECTIVE ADDITION OF NUCLEOPHILES TO HOMOCHIRAL TRICARBONYL(ETA-6-O-TRIALKYLSILYLBENZALDEHYDE)CHROMIUM(O) COMPLEXES [J].

DAVIES, SG ;

GOODFELLOW, CL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :393-407

[5] An approach to serrulatane diterpenes via endo-selective conjugate nucleophilic addition to arene-Cr(CO)3 complexes [J].

Dehmel, F ;

Lex, J ;

Schmalz, HG .

ORGANIC LETTERS, 2002, 4 (22) :3915-3918

[6] Asymmetric catalysis using planar chiral arene chromium complexes [J].

Gibson, SE ;

Ibrahim, H .

CHEMICAL COMMUNICATIONS, 2002, (21) :2465-2473

[7] Asymmetric functionalisation of tricarbonylchromium(0) complexes of arenes by non-racemic chiral bases [J].

Gibson, SE ;

Reddington, EG .

CHEMICAL COMMUNICATIONS, 2000, (12) :989-996

[8] A catalytic-enantioselective entry to planar chiral π-complexes:: Enantioselective methoxycarbonylation of 1,2-dichlorobenzene-Cr(CO)3 [J].

Gotov, B ;

Schmalz, HG .

ORGANIC LETTERS, 2001, 3 (11) :1753-1756

[9] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES [J].

HAYASHI, T ;

MISE, T ;

FUKUSHIMA, M ;

KAGOTANI, M ;

NAGASHIMA, N ;

HAMADA, Y ;

MATSUMOTO, A ;

KAWAKAMI, S ;

KONISHI, M ;

YAMAMOTO, K ;

KUMADA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) :1138-1151

[10]

HEGEDUS LS, 1999, TRANSITION METALS SY, pCH10

← 1 2 3 →