1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): Three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1607-1610

  Simoni, Daniele ^a   Rondanin, Riccardo ^a   Morini, Massimo ^a   Baruchello, Riccardo ^a   Invidiata, Francesco Paolo ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; DECALIN DERIVATIVE; GUANIDINE DERIVATIVE; PHOSPHITE; POLYMER;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION ANALYSIS; TEMPERATURE;

EID: 0034603590     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02340-0     Document Type: Article

References (18)

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3. Eisele, G.; Simchen, G. Synthesis 1978, 757.
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5. Sternbach, D.; Shibuya, M.; Jaisli, F.; Bonetti, M.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1979, 18, 634.
6. Oediger, H.; Moller, F.; Eiter, K. Synthesis 1972, 591.
7. Smith, P. A. S. In The Chemistry of Open Chain Nitrogen Compounds; Benjamin: New York, 1965, Vol. 1, Chapter 6, pp. 233-290.
8. Barton, D. H. R.; Elliott, J. D.; Géro, S. D. J. Chem. Soc., Perkin Trans. 1 1982, 2085.
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10. Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615 and references cited therein.
11. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
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15. The catalyzed addition of diethyl phosphite and nitromethane to methyl vinyl ketone, methyl acrylate and methyl crotonate proceeded by means of TBD in 85, 96, 79, 98, 95 and 72% yield, respectively.
16. Experimental procedure. The addition reactions were performed neat at 0°C: the carbonyl compound (10 mmol) and the dialkyl phosphite (or the nitroalkane) (5 ml) were mixed together in the presence of a catalytic amount (10%) of the bicyclic guanidine base, and the reaction was stirred. At the end of the reaction the mixture was diluted with diethyl ether, washed with 5% HCl, dried over sodium sulphate and distilled under vacuum.
17. Kinsaga, P. B.; Verkade, J. G. J. Org. Chem. 1999, 64, 4298 and references cited therein.
18. Dauben Jr., H. J.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson Jr., A. G. Org. Synth., Coll. Vol. 1963, 4, 221.