Azidocarboxylic acids

One-pot synthesis of aziridinyl ketones including the initial dipolar addition of azides to the ethylene bond with subsequent elimination of the nitrogen by photolysis is also possible [55, 56]. For example, in the case of azidocarboxylic acid ethyl ester 35,2-oxo-7-azabicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester 37 was synthesized via the formation of the cycloadduct 36 [55] (Scheme 1.10). 

The photodecomposition of a-azidocarboxylic acids is of interest because of the possibility of simultaneous elimination of nitrogen and carbon dioxideMoriarty and Rahman found that irradiation of a-azidobutyric acid (16) in methanol produced 25% of propionalde-... 

It has been pointed out that trichloromethyl ketones are generally available by the reaction of aldehydes with nucleophilic trichloromethide reagents followed by oxidation as well as in other ways. So, as shown in Scheme 12.60, when the trichloromethyl ketone is reduced with catecholborane in the presence of the (S)-oxazaborolidine catalyst, the corresponding (i )-secondary alcohol is produced in high enantioselectivity. Then, when the alcohol is treated with sodium hydroxide and sodium azide, the corresponding (5)-a-azidocarboxylic acid results and reduction (hydrogen [H2] in the presence of a palladium [Pd] catalyst) produces the amino acid. 

Via intermediates a-Aminocarboxylic acids from a-azidocarboxylic acid esters s. 17, 498... 

Azidoazomethine-tetrazole tautomerism 17, 467 a-Azidocarboxylic acid esters... 

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