First synthesis of a beta(2)-homoamino acid by enantioselective catalysis.
The enantioselective conjugate addition of diethylzinc to the activated nitroolefin methyl 3-nitropropenoate is efficiently catalyzed by copper(I) complexes with BINOL-based enantiopure phosphoramidite ligands. The nitroolefin moiety acts as the predominant Michael acceptor, giving rise to the unambiguous formation of 2-alkyl-3-nitro-propanoates. Moderate to excellent enantioselectivities and high chemical yields are obtained. The product can easily be transformed into a beta(2)-homoamino acid. [reaction--see text]
Rimkus
Audrius
A
Faculty of Chemistry, University of Bielefeld, PO Box 10 01 31, D-33501 Bielefeld, Germany.
Sewald
Norbert
N
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure
D000596:Amino Acids; D003300:Copper