Concepedia

Highly Chemoselective Copper-Catalyzed Conjugate Reduction of Stereochemically Labile α,β-Unsaturated Amino Ketones

Andrejs Pelšs, Esa T. T. Kumpulainen, Ari M. P. Koskinen

The Journal of Organic Chemistry · 2009 · 43 citations · 27 references

DOIFull text

Open access

Abstract

Highly chemoselective conjugate reduction of chiral alpha,beta-unsaturated amino ketones has been developed by using triisopropyl phosphite ligated copper hydride complex. The highlights of the method are wide substrate compatibility and exceptional chemoselectivity.

References

27

Selective hydride-mediated conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds using [(Ph3P)CuH]6

Wayne S. Mahoney, Donna M. Brestensky, Jeffrey M. Stryker · Journal of the American Chemical Society · 1988 · 542 citations

, , +9

Catalytic Asymmetric Reductive Michael Cyclization

Jung Woon Yang, Maria T. Hechavarria Fonseca, Benjamin List · Journal of the American Chemical Society · 2005 · 387 citations

, , +13

Hydride-mediated homogeneous catalysis. Catalytic reduction of .alpha.,.beta.-unsaturated ketones using [(Ph3P)CuH]6 and H2

Wayne S. Mahoney, Jeffrey M. Stryker · Journal of the American Chemical Society · 1989 · 196 citations

, , +16

Discovery of Potent Cell Migration Inhibitors through Total Synthesis:  Lessons from Structure−Activity Studies of (+)-Migrastatin

Jón T. Njardarson, Christoph Gaul, Dandan Shan et al. · Journal of the American Chemical Society · 2004 · 164 citations

, , +11

Lithium and potassium trialkylborohydrides. Reagents for direct reduction of .alpha.,.beta.-unsaturated carbonyl compounds to synthetically versatile enolate anions

James M. Fortunato, Bruce Ganem · The Journal of Organic Chemistry · 1976 · 156 citations

, , +9