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Organic Letters 10 (9), 1819-22 (10 Apr 2008)
Reaction of alpha methylbromo enoate with dimethyl sulfide forms dimethyl sulfide bromide salt, which adds to azodicarboxylate via [3+2] cycloaddition to afford dihydropyrazole.
Journal of the American Chemical Society 110 (19), 6487-91 (1988)
Synthesis 1981 (1), 1 (1981)
review paper on mitsunobu reaction by the man himself
Journal of the American Chemical Society 130 (6), 1804-5 (2008)
Sulfonylimidate reacts with various electrophiles such as imines (aryl, heterocyclic, aliphatic, vinylic), azodicarboxylate and methyl acrylate to generate new C-C/N bonds. High anti-selectivity is seen for mannich reactions. Treatment with DBU or Red-Al reveals ester or aldehyde, respectively, following hydrolysis of sulfonylimidate. Note the utilization of the sulfonylimidate (as opposed to carbonyls with beta-EWGs) functionality to significantly lower the pKa of the alpha proton.
Journal of the American Chemical Society 130 (7), 2158-9 (2008)
Chiral Iridium-Amido complex catalyzes asymmetric amination of alpha-cyanoacetate with azodicarboxylate. The mechanism involves deprotonation of alpha-proton by amido amine of the N-bound nitrile complex, followed by protonation of azodicarboxylate.
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