138695-41-7Relevant academic research and scientific papers
Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N, N-Dimethylacetamide
Fulton, Tyler J.,Alley, Phebe L.,Rensch, Heather R.,Ackerman, Adriana M.,Berlin, Cameron B.,Krout, Michael R.
, p. 14723 - 14732 (2018/11/23)
Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38-99% yields and 9:1-20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.
Conjugate Addition Reactions of Organosamarium Species via in Situ Transmetalation to Cu(I) Salts
Totleben, Michael J.,Curran, Dennis P.,Wipf, Peter
, p. 1740 - 1744 (2007/10/02)
Preformed organosamarium species, available by reduction of aryl or alkyl halides with SmI2, were treated with copper(I) salts to effect in situ transmetalation and conjugate addition to enones.In a series of copper(I) salts, CuI*P(OEt)3 gave best results in combination with 2 equiv of organosamarium reagent.This new method allows the multiple formation of carbon-carbon bonds through a combination of radical and cuprate chemistry.
