82830-85-1Relevant academic research and scientific papers
PREPARATION OF DIAZO AND DIAZONIUM COMPOUNDS
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Page/Page column 31-32, (2010/06/13)
A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.
Asymmetric catalysis of intramolecular N-H insertion reactions of α-diazocarbonyls
Garcia, Concepcion Fernandez,McKervey, M. Anthony,Ye, Tao
, p. 1465 - 1466 (2007/10/03)
Intramolecular N-H insertion reactions of α-diazocarbonyl substrates are catalysed by rhodium(II) carboxylates with catalyst-dependent competition with C-H insertion and β-elimination; asymmetric N-H insertion leading to a pipecolic acid derivative with ee up to 45% is achieved using chiral catalysts.
