Cobalt(I) catalysis in the diastereoselective two-step synthesis of tricyclic systems

Synthesis

Volumn , Issue 6, 2011, Pages 972-978

  Erver, Florian ^a   Hilt, Gerhard ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

alkyne; catalysis; cobalt; cycloaddition; diene; hetero Diels Alder reaction; multicomponent reaction

Indexed keywords

ALKYNE; CYCLOADDITION REACTION; CYCLOHEXADIENES; DIASTEREOSELECTIVE; DIENE; HETERO-DIELS-ALDER; HETERO-DIELS-ALDER REACTIONS; MULTI-COMPONENT REACTIONS; REGIO-SELECTIVE; TRICYCLIC PRODUCTS; TWO-STEP SYNTHESIS;

ACETYLENE; CATALYSIS; COBALT; CYCLOADDITION; OLEFINS; REGIOSELECTIVITY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

(2,4 DIMETHYLCYCLOHEXA 1,4 DIENYL)TRIMETHYLSILANE; (4 METHYLCYCLOHEXA 1,4 DIENE 1,2 DIYL)BIS(METHYLENE)DIACETATE; (4A METHYL 1 OXO 1,2,3,4A,5,8,8A,9 OCTAHYDROCYCLOPENTA[B]CHROMENE 6,7 DIYL)BIS(METHYLENE)DIACETATE; (4A METHYL 8 OXO 4,4A,5,6,7,8,9,9A OCTAHYDRO 1H XANTHENE 2,3 DIYL)BIS(METHYLENE)DIACETATE; (4A,6,6 TRIMETHYL 8 OXO 4,4A,5,6,7,8,9,9A OCTAHYDRO 1H XANTHENE 2,3 DIYL)BIS(METHYLENE)DIACETATE; 1,4 CYCLOHEXADIENE; 10A METHYL 7 PHENYL 2,3,4,8,8A,9,10A OCTAHYDRO 1H XANTHEN 1 ONE; 5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; 6,10A DIMETHYL 2,3,4,5,8,8A,9,10A OCTAHYDRO 1H XANTHEN 1 ONE; 6,7 BIS(METHOXYMETHYL) 10A METHYL 2,3,4,5,8,8A,9,10A OCTAHYDRO 1H XANTHEN 1 ONE; 6,7 BIS(METHOXYMETHYL) 3,3,10A TRIMETHYL 2,3,4,5,8,8A,9,10A OCTAHYDRO 1H XANTHEN 1 ONE; COBALT; CYCLOHEXA 1,3 DIENE; CYCLOHEXA 1,3 DIONE; CYCLOOCTA 1,3,6 TRIENE; CYCLOPENTA 1,3 DIONE; DIMETHYL 3,3,5A TRIMETHYL 1 OXO 2,3,4,5A,6,11,11A,12 OCTAHYDRO 1H CYCLOOCTA[B]CHROMENE 8,9 DICARBOXYLATE; DIMETHYL 3,3,5A,11A TETRAMETHYL 1 OXO 2,3,4,5A,6,11,11A,12 OCTAHYDRO 1H CYCLOOCTA[B]CHROMENE 8,9 DICARBOXYLATE; DIMETHYL 4A METHYL 1 OXO 1,2,3,4A,5,10,10A,11 OCTAHYDROCYCLOOCTA[E]CYCLOPENTA[B]PYRAN 7,8 DICARBOXYLATE; DIMETHYL 4A,10A DIMETHYL 1 OXO 1,2,3,4A,5,10,10A,11 OCTAHYDROCYCLOOCTATE[E]CYCLOPENTA[B]PYRAN 7,8 DICARBOXYLATE; DIMETHYL 5 METHYLCYCLOOCTA 2,5,8 TRIENE 1,2 DICARBOXYLATE; DIMETHYL 5,6 DIMETHYLCYCLOOCTA 2,5,8 TRIENE 1,2 DICARBOXYLATE; DIMETHYL 5A METHYL 1 OXO 2,3,4,5A,6,11,11A,12 OCTAHYDRO 1H CYCLOOCTA[B]CHROMENE 8,9 DICARBOXYLATE; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; KNOEVENAGEL CONDENSATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 79952447114     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258433     Document Type: Article

References (23)

1. For recent reviews, see:, Leboeuf D, Gandon V, Malacria M, In Handbook of Cyclization Reactions Vol. 1 Ma S Wiley-VCH Weinheim 2009 367
2. Galan B R., Rovis T, Angew. Chem. Int. Ed. 2009 48 2830
3. Omae I, Appl. Organomet. Chem. 2008 22 149
4. Hess W, Treutwein J, Hilt G, Synthesis 2008 3537
5. Omae I, Appl. Organomet. Chem. 2007 21 318
6. Kotha S, Brahmachary E, Lahiri K, Eur. J. Org. Chem. 2005 4741
7. Malacria M, Aubert C, Renaud J L., In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 1 Lautens M Trost B M. Thieme Stuttgart 2001 439
8. Saito S, Yamamoto Y, Chem. Rev. 2000 100 2901
9. Hilt G, Paul A, Harms K, J. Org. Chem. 2008 73 5187
10. Hilt G, Paul A, Hengst C, Synthesis 2009 3305
11. Hilt G, Hess W, Harms K, Synthesis 2008 75
12. Treutwein J, Hilt G, Angew. Chem. Int. Ed. 2008 47 6811
13. Hilt G, Janikowski J, Angew. Chem. Int. Ed. 2008 47 5243 For alternative cobalt-catalysed reactions involving cyclopentadienyl cobalt-type catalyst systems, see reference 1.
14. For the application of cyclic and acyclic 1,4-dienes as synthons for 1,3-dicarbonyl compounds, see:, Kersten L, Roesner S, Hilt G, Org. Lett. 2010 12 4920
15. Hilt G, Arndt M, Weske D F., Synthesis 2010 1321
16. Hilt G, Weske D F., Chem. Soc. Rev. 2009 38 3082
17. Danz M, Hilt G, Adv. Synth. Catal. 2011 in press
18. Auvinet A.-L, Harrity J P. A., Hilt G, J. Org. Chem. 2010 75 3893
19. Hilt G, Janikowski J, Org. Lett. 2009 11 773
20. Hilt G, Danz M, Synthesis 2008 2257
21. Mörschel P, Janikowski J, Hilt G, Frenking G, J. Am. Chem. Soc. 2008 130 8952
22. Hilt G, Janikowski J, Hess W, Angew. Chem. Int. Ed. 2006 45 5204
23. Koser S, Hoffmann H M. R., Heterocycles 1994 37 661