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Synthesis 2015; 47(08): 1170-1180
DOI: 10.1055/s-0034-1380148
DOI: 10.1055/s-0034-1380148
paper
Synthesis of Acyclic Polycarbonyl Compounds via Ozonolysis of Cyclohexa-1,4-dienes
Further Information
Publication History
Received: 09 December 2014
Accepted after revision: 14 January 2015
Publication Date:
19 February 2015 (online)
Abstract
Cobalt-catalyzed Diels–Alder reaction of 2-(trimethylsiloxy)buta-1,3-dienes with alkynes gives substituted cyclohex-3-en-1-ones that were converted into polycarbonyl derivatives upon ozonolysis. Wittig olefination of ketoaldehydes gave unsaturated polycarbonyl derivatives or alternatively the ketoaldehydes were reacted with primary and secondary amines to give vinylogous amides. 2,7-Didiazo-1-phenylnonane-1,3,6,8-tetraone underwent double diazo-transfer reaction at the 1,3-dicarbonyl subunits by rhodium-catalyzed cyclization to give the cyclohex-2-ene-1,4-dione backbone.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380148.
- Supporting Information
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References
- 1a Amat M, Griera R, Fabregat R, Molins E, Bosch J. J. Org. Chem. 2010; 75: 3797
- 1b Calo F, Richardson F, Barrett AG. M. Org. Lett. 2009; 11: 4910
- 1c Amat M, Griera R, Fabregat R, Molins E, Bosch J. Angew. Chem. Int. Ed. 2008; 47: 3348
- 1d Rubin MB, Gleiter R. Chem. Rev. 2000; 100: 1121
- 1e Griffin DA, Leeper FJ, Staunton J. J. Chem. Soc., Perkin Trans. 1 1984; 1035
- 2 Tarun EI, Rubinov DB, Metelitza DI. Appl. Biochem. Microbiol. 2005; 41: 12
- 3a Kersten L, Hilt G. Adv. Synth. Catal. 2012; 354: 863
- 3b Hilt G, Arndt M, Weske D. Synthesis 2010; 1321
- 3c Kersten L, Roesner S, Hilt G. Org. Lett. 2010; 12: 4920
- 3d Hilt G, Weske DF. Chem. Soc. Rev. 2009; 38: 3082
- 4a Hilt G. Chem. Rec. 2014; 14: 386
- 4b Hilt G. Synlett 2011; 1654
- 4c Hilt G, Korn TJ. Tetrahedron Lett. 2001; 42: 2783
- 4d Hilt G, du Mesnil F.-X, Lüers S. Angew. Chem. Int. Ed. 2001; 40: 387
- 5a Kuttner JR, Warratz S, Hilt G. Synthesis 2010; 1293
- 5b Hilt G, Smolko KI, Lotsch BV. Synlett 2002; 1081
- 6 Erver F, Kuttner JR, Hilt G. J. Org. Chem. 2012; 77: 8375
- 7 Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 8a Zhou CC, Hill DR. Magn. Reson. Chem. 2007; 45: 128
- 8b Raczynska ED, Kosinska W, Osmialowski B, Gawinecki R. Chem. Rev. 2005; 105: 3561
- 8c Rappoport Z. The Chemistry of Enols . Wiley; Chichester: 1990
- 9a Mehta G, Muthusamy S. Tetrahedron 2002; 58: 9477
- 9b Hodgson DM, Pierard FY. T. M, Stupple PA. Chem. Soc. Rev. 2001; 30: 50
- 9c Singh VK, DattaGupta A, Sekar G. Synthesis 1997; 137
- 9d Li A.-H, Dai L.-X, Aggarwal VK. Chem. Rev. 1997; 97: 2341
- 9e Ishiguro K, Ikeda M, Sawaki Y. J. Org. Chem. 1992; 57: 3057
- 9f Padwa A, Hornbuckle SF. Chem. Rev. 1991; 91: 263
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