Application of the Suzuki reaction to the asymmetric desymmetrisation of 1,2-and 1,3-disubstituted bulky cobalt metallocenes

被引：23

作者：

Bergin, Enda ^{[1
]}

Hughes, David L. ^{[1
]}

Richards, Christopher J. ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem, Norwich NR4 7TJ, Norfolk, England

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 11-12期

基金：

英国工程与自然科学研究理事会;

关键词：

ORGANOMETALLIC PI-COMPLEXES; PLANAR CHIRALITY; ENANTIOSELECTIVE METHOXYCARBONYLATION; DIASTEREOSELECTIVE PALLADATION; OXAZOLINE PALLADACYCLES; ABSOLUTE CONFIGURATIONS; FERROCENE DERIVATIVES; REAGENTS; STEREOCHEMISTRY; REARRANGEMENT;

D O I：

10.1016/j.tetasy.2010.05.012

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of (eta(5)-cyclopentadienyl)(eta(4)-tetraphenylcyclobutadiene)cobalt with Hg(OAc)(2) (2.3 equiv) in 1:1 MeOH/CH(2)Cl(2) followed by the addition of LiCl resulted in the formation of (eta(5)-1,2-dichloromercuricyclopentadienyl)(eta(4)-tetraphenylcyclobutadiene)cobalt (33%) and its 1,3-isomer (6%). Following conversion into their corresponding diiodides these compounds were desymmetrised by Suzuki reactions with ArB(OH)(2) employing [(R)-BINAP]PdCl(2), with the highest ee of 24% being obtained for (eta(5)-1-iodo-3-(2-methoxyphenyl)cyclopentadienyl)(eta(4)-tetraphenylcyclobutadiene)cobalt. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1619 / 1623

页数：5

共 32 条

[1] Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].

Arrayas, Ramon Gomez ;

Adrio, Javier ;

Carretero, Juan Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715

[2] First planar chiral bidentate ligand based on a (η5-cyclopentadienyl)(η4-cyclobutadiene) cobalt backbone:: high efficiency in enantioselective palladium-catalyzed allylic substitutions [J].

Arrayás, RG ;

Mancheño, OG ;

Carretero, JC .

CHEMICAL COMMUNICATIONS, 2004, (14) :1654-1655

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

Böttcher, A ;

Schmalz, HG .

SYNLETT, 2003, (11) :1595-1598

[4] Synthesis of 1′-substituted derivatives of 1,2,3,4,5-pentaphenylferrocene [J].

Butler, DCD ;

Richards, CJ .

ORGANOMETALLICS, 2002, 21 (24) :5433-5436

[5] Biocatalytic procedure for obtaining all four diastereoisomers of 1-(1-hydroxyethyl)-3-ethylferrocene: synthons for chiral 1,3-disubstituted ferrocenes [J].

D'Antona, N ;

Lambusta, D ;

Morrone, R ;

Nicolosi, G ;

Secundo, F .

TETRAHEDRON-ASYMMETRY, 2004, 15 (24) :3835-3840

[6]

Dai L.X., 2009, Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications

[7] STEREOCHEMISTRY OF METALLOCENES .24. (FERROCENES 45) . OPTICALLY ACTIVE(3) AND (3)(3)FERROCENOPHANES .1. SYNTHESES OPTICAL RESOLUTION AND ABSOLUTE CONFIGURATIONS [J].

FALK, H ;

HOFER, O ;

SCHLOGL, K .

MONATSHEFTE FUR CHEMIE, 1969, 100 (02) :624-&

[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] HIGHLY GENERAL STEREO-SELECTIVE, REGIO-SELECTIVE, AND CHEMO-SELECTIVE SYNTHESIS OF TERMINAL AND INTERNAL CONJUGATED ENYNES BY PD-CATALYSED REACTION OF ALKYNYLZINC REAGENTS WITH ALKENYL HALIDES [J].

KING, AO ;

OKUKADO, N ;

NEGISHI, EI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (19) :683-684

[10] PERCHLORIC ACID CATALYZED AROMATIC MERCURATION IN ACETIC ACID SOLUTION .I. ELECTROPHILIC REAGENTS [J].

KRESGE, AJ ;

DUBECK, M ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) :745-&

← 1 2 3 4 →