1253944-16-9Relevant academic research and scientific papers
One-pot synthesis of vicinal aminoalkanols from sugar aldehydes
Soengas, Raquel G.,Silva, Artur M.S.
, p. 3425 - 3431 (2013/05/08)
A novel synthetic method of carbohydrate derived vicinal aminoalcohols, from sugar aldehydes and bromonitroalkanes, has been developed. It involves an indium-catalyzed one-pot Henry reaction and nitro group reduction, and proceeds with a remarkably high anti-selectivity. The reaction of the intermediate aminoalcohols with alkylating agents furnished the corresponding carbohydrate-based tertiary aminoalcohols with excellent stereoselectivity. This very simple methodology allows easy access to families of N,N-dialkylated vicinal aminoalkanols, useful intermediates in the synthesis of derivatives of biological interest and sugar-based stereodifferentiating agents for asymmetric catalysis.
Synthesis of sugar-derived 2-nitroalkanols via Henry reaction promoted by samarium diiodide or indium
Rodríguez-Solla, Humberto,Alvaredo, Noemí,Soengas, Raquelg.
supporting information, p. 2083 - 2086 (2012/11/13)
We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI 2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes. Georg Thieme Verlag Stuttgart New York.
Indium-mediated reaction of 1-bromo-1-nitroalkanes with aldehydes: Access to 2-nitroalkan-1-ols
Soengas, Raquel G.,Estevez, Amalia M.
experimental part, p. 5190 - 5196 (2010/11/02)
A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel sugar-derived 2,2-dialkyl-2-nitroalkan-1-ols for the preparation of branched iminosugar derivatives was demonstrated by the preparation of a hydroxymethyl branched polyhydroxylated azepane.
