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

Daniele Simoni,Riccardo Rondanin,Massimo Morini,Riccardo Baruchello,Francesco Paolo Invidiata

doi:10.1016/s0040-4039(99)02340-0

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

Daniele Simoni, Riccardo Rondanin + Show 3 more

https://doi.org/10.1016/s0040-4039(99)02340-0

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Journal: Tetrahedron Letters	Publication Date: Mar 1, 2000
Citations: 123

Affiliation: University of Palermo

#Addition Of Phosphites #Henry Reaction + Show 8 more

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Abstract

The 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its 7-methyl derivative (MTBD) have been proven to be of great synthetic utility as catalysts in the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to a variety of carbonyl compounds. The catalysts were in many cases superior to the parent tetramethylguanidine (TMG). In general the reaction proceeds in a few minutes at 0°C. The polymer-supported-TBD (P-TBD) was also proven to be an efficient promoter of the above cited nucleophilic additions.

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