Journal
ORGANIC LETTERS
Volume 3, Issue 19, Pages 2989-2992Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol016324p
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[GRAPHICS] N-Tosyl diazoketamines were prepared by addition of the ethyl alpha -diazoacetate anion to N-sulfonylimines. The diazo decomposition of the diazoketamines with Rh-2(OAc)(4) complex resulted in aryl migration to give alpha -aryl-beta -enamino esters in good yields and high stereoselectivity. The effect of the catalysts on the migratory aptitude of 1,2-aryl over 1,2-hydride migration was studied. A reaction mechanism involving a bridged phenonium ion is proposed.
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