Efficient Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to aromatic and aliphatic acyclic nitroalkenes.
An efficient and highly enantioselective (up to 95% ee) Cu-catalyzed method for asymmetric conjugate addition (ACA) of alkylzinc reagents to acyclic disubstituted nitroalkenes is presented. Reactions are typically effected at ambient temperature in the presence of 2 mol % chiral dipeptide phosphine and 1 mol % (CuOTf)(2).C(6)H(6). Nitroalkenes bearing aromatic as well as aliphatic substituents readily undergo asymmetric additions. [reaction: see text]
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Dawn M
DM
Mampreian
Amir H
AH
Hoveyda
D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003516:Cycloparaffins / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008024:Ligands; D009574:Nitro Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
D000475:Alkenes; D000588:Amines; D003516:Cycloparaffins; D007202:Indicators and Reagents; D008024:Ligands; D009574:Nitro Compounds; D009942:Organometallic Compounds; D003300:Copper; D015032:Zinc