167968-03-8Relevant academic research and scientific papers
β-Oxy-α-Diazo Carbonyl Compounds. IV. Reaction with Triethyl borane. The influence of the Oxy Group in the Regio- and Stereo-controlled Alkylation on the Diazo Carbon
Lopez-Herrera, Fidel J.,Sarabia-Garcia, Francisco
, p. 2851 - 2854 (1995)
The reactions of chiral β-oxy-α-diazocarbonyl compounds with triethylborane were studied.The results of the reactions depend on the particular group used to protect the β-hydroxyl function.Thus, hindered protecting groups lead to N-alkylation of the diazo compound.On the other hand, the product with a free hydroxyl group, undergoes C-alkylation in a good yield with full stereoselectivity.
Reactions of monosaccharide derivatives with diazocarbonyl compounds. Reactivity and synthetic applications
Sarabia Garcia, Francisco,Pedraza Cebrian, Gracia Maria,Heras Lopez, Alfonso,Lopez Herrera, F. Jorge
, p. 6867 - 6896 (1998)
The reaction of monosaccharide derivatives with different stabilized diazo compounds is reported. Studies on the reactivity of the condensation products have been undertaken, finding out novel transformations of β-oxy- α-diazo carbonyl compounds with synthetic applications. Thus, a stereoselective Wolff rearrangement provided syn 2-hydroxy-1-methyl compounds, which represent macrolide type structural subunits. On the other hand, rhodium (II) mediated rearrangements of β-acetoxy-α-diazo carbonyl compounds derived from monosaccharides have loci to an efficient synthesis of the natural aldonic acids KDG and DAH.
