Asymmetric Mannich reactions with in situ generation of carbamate-protected imines by an organic catalyst.
The instability of carbamate-protected alkyl imines has greatly hampered the development of catalytic asymmetric Mannich reactions suitable for the synthesis of optically active carbamate-protected chiral alkyl amines. A highly enantioselective Mannich reaction with in situ generation of carbamate-protected imines from stable alpha-amido sulfones catalyzed by an organic catalyst was developed. This reaction provides a concise and highly enantioselective route converting aromatic and aliphatic aldehydes into optically active aryl and alkyl beta-amino acids. [reaction: see text].
Song
Jun
J
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Shih
Hui-Wen
HW
Deng
Li
L
D000596:Amino Acids / Q000138:chemical synthesis; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D002219:Carbamates; D002930:Cinchona Alkaloids; D007097:Imines