Cationic cobalt(I) catalysts for the asymmetric cyclocarbonylation of 1,6-enynes

Chirality

Volumn 17, Issue 7, 2005, Pages 353-356

  Schmid, Thomas M ^a   Gischig, Sebastian ^a   Consiglio, Giambattista ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

2+2+1 cycloaddition; Carbonylation; Cyclopentenones; MeO Biphep; Pauson Khand reaction

Indexed keywords

(6,6' DIMETHOXYBIPHENYL 2,2' DIYL)BIS(DIPHENYLPHOSPHINE); 4,4 BIS(CARBOETHOXY)HEPT 5 EN 1 YNE; COBALT COMPLEX; CYCLOPENTENONE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CARBONYLATION; CYCLOADDITION; ENANTIOSELECTIVITY; PAUSON KHAND REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 22844452110     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20173     Document Type: Article

References (15)

1. Gibson SE, Lewis SE, Mainolfi N. Transition metal-mediated routes to cyclopentenones. J Organomet Chem 2004;689:3873-3890.
2. Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domínguez G, Pérez-Castels J. The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules. Chem Soc Rev 2004;33:32-42.
3. Gibson SE, Stevenazzi A. The Pauson-Khand reaction: the catalytic age is here! Angew Chem Int Ed 2004;42:1800-1810.
4. Hicks FA, Buchwald SL. An intramolecular titanium-catalyzed asymmetric Pauson-Khand type reaction. J Am Chem Soc 1999;121: 7026-7033.
5. (a) Hiroi K, Watanabe T, Kawagishi R, Abe I. Asymmetric catalytic Pauson-Khand reactions with chiral phosphine ligands: dramatic effects of substituents in 1,6 enyne systems. Tetrahedron Lett 2000;41: 891-895.
6. (b) Hiroi K, Watanabe T, Kawagishi R, Abe I. Catalytic use of chiral phosphine ligands in asymmetric Pauson-Khand reactions. Tetrahedron: Asymmetry 2000;11:797-808.
7. Jeong N, Sung BK, Choi YK. Rhodium (I)-catalyzed asymmetric intramolecular Pauson-Khand-type reaction. J Am Chem Soc 2000;122: 6771-6772.
8. Shibata T, Takagi K. Iridium-chiral diphosphine complex catalyzed highly enantioselective Pauson-Khand-type reaction. J Am Chem Soc 2000;122:9852-9853.
9. Schmid TM, Consiglio G. Mechanistic and stereochemical aspects of the asymmetric cyclocarbonylation of 1,6-enynes with rhodium catalysts. Chem Commun 2004;2318-2319.
10. Schmid TM, Consiglio G. Asymmetric cyclocarbonylation of 1,6-enynes with cobalt catalysts. Tetrahedon: Asymmetry 2004;15: 2205-2208.
11. Gibson SE, Lewis SE, Loch JA, Steed JW, Tozer MJ. Identification of an asymmetric Pauson-Khand precatalyst. Organometallics 2003;22: 5382-5384.
12. Schmid R, Foricher J, Cereghetti M, Schonholzer P. Axially dissymmetric diphosphines in the biphenyl series. Synthesis of (6,6′-dimethoxybiphenyl- 2,2′-diyl)bis(diphenylphosphine) (MeO-Biphep) and analogs via an ortholithiation iodination Ullmann-reaction approach. Helv Chim Acta 1991;74:370-389.
13. Lee BY, Chung YK, Jeong N, Lee Y, Hwang SH. (Indenyl)cobalt(I)-catalyzed cocyclization of alkyne, alkene and carbon monoxide to cyclopentenones. J Am Chem Soc 1994;116:8793-8794.
14. Kobayashi T, Koka Y, Narasaka K. The rhodium-catalyzed Pauson-Khand reaction. J Organomet Chem 2001;624:73-87.
15. Schumann H. Zur Verwendung von Ferricenium-Kationen als selektivem Oxidationsmittel in der metallorganischen Chemie. J Organomet Chem 1986;304:341-351.