A. Katritzky, Khalid Widyan, Kapil Gyanda
Aug 12, 2008
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0
Influential Citations
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ChemInform
Abstract
Sulfonyl azides (RSO2N3) are valuable reagents for diazo transfer to the a-methylene position of carbonyl compounds such as b-oxo esters and oxo sulfones.1,2 Charette and co-workers reported trifluoromethanesulfonyl azide (triflyl azide, 1), a highly electrophilic diazo-transfer reagent, gives good results with activated acetic acid esters and ketones (Figure 1).3,4 3-Pyridinesulfonyl azide (2) appears to be more efficient for radical azidating than 4(methoxycarbonyl)benzenesulfonyl azide and 3and 4carboxybenzenesulfonyl azides.5,6 Sulfonyl azides [especially 2,4,6-triisopropylbenzenesulfonyl azide (3)] have been used in the a-azidation of amide enolates and ester enolates in the synthesis of a-amino acid derivatives.7