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

作者：Pennaforte Erica V; Costa Jeronimo S; Silva Cristiane A; Saraiva Marcelo C; Pereira Vera L P^*

来源：Letters in Organic Chemistry, 2009, 6(2): 110-114.

DOI：10.2174/157017809787582771

• Henry reaction
• nitronate ions
• nitroalkanes
• tetrabutylammonium fluoride
• gamma-lactones

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 gamma-lactone 2, a potential precursor of bioactive beta-aminoacids, was also investigated.

• 出版日期2009-3