A Study of the Influence of Base, Temperature and Reaction Time in Nitroaldol Reactions Using (R)-(+)-Glyceraldehyde Acetonide: Diastereoselective Synthesis of (4R, 5R)-Dihydro-5-((R)-1,2-Dihydroxyethyl)-4-Nitrofuran- 2(3H)-one

Title: A Study of the Influence of Base, Temperature and Reaction Time in Nitroaldol Reactions Using (R)-(+)-Glyceraldehyde Acetonide: Diastereoselective Synthesis of (4R, 5R)-Dihydro-5-((R)-1,2-Dihydroxyethyl)-4-Nitrofuran- 2(3H)-one

Volume: 6 Issue: 2

Author(s): Erica V. Pennaforte, Jeronimo S. Costa, Cristiane A. Silva, Marcelo C. Saraiva and Vera L.P. Pereira

Affiliation:

Keywords: Henry reaction, nitronate ions, nitroalkanes, tetrabutylammonium fluoride, γ-lactones

Abstract: The Henry reaction between the nitroalkanes 6-11 and (R)-(+)-glyceraldehyde acetonide (1), was investigated in respect to the variation of the base, temperature and reaction time. Nitroalcohols 5a-f were obtained in good yields (70- 85%) and moderate to good anti-selectivities (50-79%). The transformation of the nitroalcohol 5a,b in title γ-lactone 2, a potential precursor of bioactive β-aminoacids, was also investigated.

Cite this article as:

Pennaforte V. Erica, Costa S. Jeronimo, Silva A. Cristiane, Saraiva C. Marcelo and Pereira L.P. Vera, A Study of the Influence of Base, Temperature and Reaction Time in Nitroaldol Reactions Using (R)-(+)-Glyceraldehyde Acetonide: Diastereoselective Synthesis of (4R, 5R)-Dihydro-5-((R)-1,2-Dihydroxyethyl)-4-Nitrofuran- 2(3H)-one, Letters in Organic Chemistry 2009; 6 (2) . https://dx.doi.org/10.2174/157017809787582771