Does anyone have anything on alpha-alkylation of nitroalkanes? Looking for information on melatonin, I came across:
Snyder, H.R. & Katz, L. (1947). "The alkylation of aliphatic nitro compounds with gramine. A new synthesis of tryptamines." J. Am. Chem. Soc. 69, pp. 3140-3142
Lyttle, D.A. & Weisblat, D.I. (1947). "The chemistry of nitroacetic acid and its esters. I. The alkylation of alkylnitroacetates with gramine." J. Am. Chem. Soc. 69, pp. 2118-2119
Snyder and Katz refluxed 3-indolylmethyl dimethylamine or its methiodide with excess nitromethane, nitroethane or ethyl nitroacetate, in the presence of solid NaOH as a catalyst, and obtained mostly the di-(indolylmethyl) derivatives. Lyttle and Weisblat refluxed the 3-indolylmethyl dimethylamine with ethyl nitroacetate in xylene without any catalyst, and got the monoalkyl product, which was hydrogenated to tryptophan ethyl ester. With NaOH as a catalyst, the product was again the dialkyl derivative.
Those papers are a long time back. There must have been some more recent work. How would a benzyl trimethylammonium iodide derivative react with nitroethane or nitroethane for instance?