A Facile Reaction of Unactivated Imines with Telluronium Allylide . Highly Stereoselective Synthesis of Vinylaziridines
Supporting Information General methods. Infrared spectra were recorded on a Nicolet AVATAR-360 spectrometer. H NMR and C NMR spectra were recorded at Bruker AM-300 instruments. Low resolution mass spectra (m/z) were recorded on HP5989A. High-resolution mass spectra were recorded on Concept 1H or MALDI/DHB. Microanalyses were performed using a Elemantar Vario EL. All reaction flasks were dried by flame. And all reactions were carried out under argon unless otherwise noted. THF and toluene were dried by distilled over sodium-benzophenone ketyl prior to use. N-aryl imines and -amidoalkyl-p-tolyl sulfones were prepared according to literature methods.
The Wittig Rearrangement
In 1942 Wittig and Lohmann described the isomerization of α-lithiated ethers (2; R = Me or CH2Ph) to skeletally rearranged lithio alkoxides (3; equation 1).1 Subsequent work by Wittig and others established that a variety of ethers undergo the Wittig rearrangement, provided the α-anion is stabilized by an aryl substituent. Of the several mechanisms proposed for this reaction a sequence involving homolysis of the anion intermediate (5), followed by recombination of the radical and radical anion fragments (equation 2) best accommodates the experimental findings.1–4
Stereochemistry of the 1,2-Wittig rearrangement: A synthesis of syn-1,3-diol monoethers
Etude de la transposition d'allyloxymethyl-4 dimethyl-2,2 dioxannes-1,3 et -dioxolannes-1,3 et d'allyloxymethyl-2 perhydrofurannes en α-vinyl dimethyl-2,2 dioxanne-1,3- et -dioxolanne-1,3ethanols-4 et en α-vinyl perhydro furanneethanols-2. Diastereoselectivite