Iron(II)/copper(I)-mediated stereoselective carbozincation of ynamides. One-pot synthesis of α-allyl-tetrasubstituted-enamides
The iron(II) chloride- and copper(I) iodide-mediated carbozincation of a panel of substituted ynamides is described in this article. The reaction is totally regio- and stereoselective. Experiments showed that the reaction mediated with Fe(II) was more substrate dependent than the reaction performed with Cu(I). Interestingly, in the presence of allylbromide, stereoselective carboallylation can be achieved for the first time in a one-pot procedure, leading to skipped dienamides.
N -alkynyl imides (ynimides): Synthesis and use as a variant of highly labile ethynamine
This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.
Sueda, Takuya,Oshima, Ayumi,Teno, Naoki
supporting information; experimental part
p. 3996 - 3999
(2011/10/01)
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