Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones

Journal of the American Chemical Society

Volumn 125, Issue 28, 2003, Pages 8432-8433

  Hachisu, Yoshifumi ^a   Bode, Jeffrey W ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; BENZOIN; KETONE DERIVATIVE; TERTIARY AMINE;

ARTICLE; CATALYSIS; COMBINATORIAL CHEMISTRY; COVALENT BOND; CROSS LINKING; HYDROLYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0038375618     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035308f     Document Type: Article

References (25)

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18. For examples of intramolecular benzoin reactions, see: (a) Gleiter, R.; Krennich, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 449-450. (b) Cookson, R. C.; Lane, R. M. J. Chem. Soc., Chem. Commun. 1976, 804-805.
19. For examples of intramolecular benzoin reactions, see: (a) Gleiter, R.; Krennich, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 449-450. (b) Cookson, R. C.; Lane, R. M. J. Chem. Soc., Chem. Commun. 1976, 804-805.
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21. At the current stage of development, we have found this reaction to be viable for a variety of keto-aldehydes, including aliphatic systems. Further reaction development to exclude the competing aldol processes as well as mechanistic studies are underway and will be reported in due course.
22. For enantioselective catalysts for intermolecular benzoin and intramolecular Stetter reactions, see: (a) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745. (b) Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
23. For enantioselective catalysts for intermolecular benzoin and intramolecular Stetter reactions, see: (a) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745. (b) Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
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25. For the use of imines as electrophiles in a benzoin-type reaction, see: (a) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696-9697. (b) Katritzky, A. R.; Cheng, D.; Musgrave, R. P. Heteroycles 1996, 42, 273-281.