A formal enantioselective acetate Mannich reaction: the nitro functional group as a traceless agent for activation and enantiocontrol in the synthesis of beta-amino acids.
A two-step procedure involving the enantioselective addition of alpha-nitro esters to imines, followed by reductive denitration, provides a convenient new enantioselective synthesis of beta-amino acids. Specifically, beta-phenyl alanine derivatives with up to 98% ee are formed in good yield (64-88%) over two steps. The utility of the approach is demonstrated through the first enantioselective synthesis of the key beta-amino acid of (+)-chaenorhine.
Shen
Bo
B
Department of Chemistry & Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
Johnston
Jeffrey N
JN
D000085:Acetates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000596:Amino Acids; D004952:Esters; D008352:Mannich Bases; D017672:Nitrogen Compounds