683246-82-4Relevant academic research and scientific papers
Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes
Jouvin, Kevin,Coste, Alexis,Bayle, Alexandre,Legrand, Frederic,Karthikeyan, Ganesan,Tadiparthi, Krishnaji,Evano, Gwilherm
, p. 7933 - 7947 (2013/01/16)
Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing
Synthesis of 1,2-amino alcohols by sigmatropic rearrangements of 3-(N-Tosylamino)allylic alcohol derivatives
Barbazanges, Marion,Meyer, Christophe,Cossy, Janine,Turner, Peter
scheme or table, p. 4480 - 4495 (2011/06/24)
Sigmatropic rearrangements of 3-(N-tosylamino)allylic alcohol derivatives, a particular subclass of functionalized enamides, have been investigated. Whereas the presence of the nitrogen atom alters the stereochemical outcome of Ireland-Claisen rearrangeme
Stereoselective synthesis of 1,2-aminoalcohols by [2,3]-wittig rearrangements
Barbazanges, Marion,Meyer, Christophe,Cossy, Janine
, p. 3245 - 3248 (2008/02/12)
[2,3]-Wittig rearrangements of (E)-3-aza-allylic alcohol derivatives can provide access to functionalized 1,2-aminoalcohols with high syn or anti diastereoselectivity depending on the anionic stabilizing group (amide or alkyne). American Chemical Society.
Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides
Zhang, Yanshi,Hsung, Richard P.,Tracey, Michael R.,Kurtz, Kimberly C. M.,Vera, Eymi L.
, p. 1151 - 1154 (2007/10/03)
(Equation presented) A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO4·5H2O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.
