Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents of α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes

✍ Scribed by Jos P.G. Versleijen; Albert M. van Leusen; Ben L. Feringa

• Book ID: 104261901
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 241 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01118-1

✦ Synopsis

The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Zmixtures of et,13-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) were obtained with structurally rigid 3-nitrocoumarins, leading to a new route to optically active 13-aryl-nitroalkanes.