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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 6, Issue 2, 2009

Page: [110 - 114] Pages: 5

DOI: 10.2174/157017809787582771

Price: $65


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.

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

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