Unusual coupling reactions of aldehydes and alkynes: A novel preparation of substituted phthalic acid derivatives by automated synthesis

Chemistry - A European Journal

Volumn 9, Issue 10, 2003, Pages 2273-2281

  Von Wangelin, Axel Jacobi ^a   Neumann, Helfried ^a   Gördes, Dirk ^a   Klaus, Stefan ^a   Jiao, Haijun ^a   Spannenberg, Anke ^a   Krüger, Thomas ^a   Wendler, Christian ^a   Thurow, Kerstin ^a   Stoll, Norbert ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Automated synthesis; Diels Alder reaction; Domino reaction; Multicomponent reaction; Organocatalysis

Indexed keywords

ADDITION REACTIONS; CARBOXYLIC ACIDS; CATALYSTS; COMPOSITION; CONDENSATION; DERIVATIVES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

COUPLING REACTIONS;

ALDEHYDES;

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; PHTHALIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; CYCLOADDITION; DIELS ALDER REACTION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0038509974     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204668     Document Type: Article

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36. -3. CCDC-195184 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).
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48. Similar reactions that involve dominating 1,4-syn eliminations have been reported: a) S. J. Cristol, Acc. Chem. Res. 1971, 4, 393-400; b) R. K. Hill, M. G. Bock, J. Am. Chem. Soc. 1978, 100, 637-639; c) R. J. Moss, R. O. White, B. Rickborn, J. Org. Chem. 1985, 50, 5132-5139; d) R. J. Moss, B. Rickborn, J. Org. Chem. 1986, 51, 1992-1996; e) J. J. Rabasco, S. R. Kass, J. Org. Chem. 1993, 58, 2633-2636; f) S. Gronert, S. R. Kass, J. Org. Chem. 1997, 62, 7991-8000.
49. Similar reactions that involve dominating 1,4-syn eliminations have been reported: a) S. J. Cristol, Acc. Chem. Res. 1971, 4, 393-400; b) R. K. Hill, M. G. Bock, J. Am. Chem. Soc. 1978, 100, 637-639; c) R. J. Moss, R. O. White, B. Rickborn, J. Org. Chem. 1985, 50, 5132-5139; d) R. J. Moss, B. Rickborn, J. Org. Chem. 1986, 51, 1992-1996; e) J. J. Rabasco, S. R. Kass, J. Org. Chem. 1993, 58, 2633-2636; f) S. Gronert, S. R. Kass, J. Org. Chem. 1997, 62, 7991-8000.
50. Similar reactions that involve dominating 1,4-syn eliminations have been reported: a) S. J. Cristol, Acc. Chem. Res. 1971, 4, 393-400; b) R. K. Hill, M. G. Bock, J. Am. Chem. Soc. 1978, 100, 637-639; c) R. J. Moss, R. O. White, B. Rickborn, J. Org. Chem. 1985, 50, 5132-5139; d) R. J. Moss, B. Rickborn, J. Org. Chem. 1986, 51, 1992-1996; e) J. J. Rabasco, S. R. Kass, J. Org. Chem. 1993, 58, 2633-2636; f) S. Gronert, S. R. Kass, J. Org. Chem. 1997, 62, 7991-8000.
51. Similar reactions that involve dominating 1,4-syn eliminations have been reported: a) S. J. Cristol, Acc. Chem. Res. 1971, 4, 393-400; b) R. K. Hill, M. G. Bock, J. Am. Chem. Soc. 1978, 100, 637-639; c) R. J. Moss, R. O. White, B. Rickborn, J. Org. Chem. 1985, 50, 5132-5139; d) R. J. Moss, B. Rickborn, J. Org. Chem. 1986, 51, 1992-1996; e) J. J. Rabasco, S. R. Kass, J. Org. Chem. 1993, 58, 2633-2636; f) S. Gronert, S. R. Kass, J. Org. Chem. 1997, 62, 7991-8000.