Highly Enantioselective Synthesis of α-Amino Acid Derivatives by an NHC-Catalyzed Intermolecular Stetter Reaction

• Published in: Angewandte Chemie International Edition Vol. 50; no. 6; pp. 1410 - 1414
• Main Authors: Jousseaume, Thierry, Wurz, Nathalie E., Glorius, Frank
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 07.02.2011; WILEY‐VCH Verlag; Wiley
• Subjects: amino acids; Amino Acids - chemical synthesis; Amino Acids - chemistry; asymmetric catalysis; Catalysis; Chemistry; Chemistry, Multidisciplinary; Heterocyclic Compounds - chemistry; Methane - analogs & derivatives; Methane - chemistry; N-heterocyclic carbene; organocatalysis; Physical Sciences; protonation; Science & Technology; Stereoisomerism; N-heterocyclic carbene; protonation; ASYMMETRIC-SYNTHESIS; HYDROGEN-ATOM TRANSFER; ENOLATE PROTONATIONS; amino acids; ALDEHYDES; asymmetric catalysis; CONJUGATE ADDITION-PROTONATION; CASCADE REACTION; organocatalysis; NONADJACENT STEREOCENTERS; 1,4-ADDITION/ENANTIOSELECTIVE PROTONATION; ACTIVATED DOUBLE-BONDS

PROTONtype: An NHC‐catalyzed (NHC=N‐heterocyclic carbene), highly asymmetric intermolecular Stetter reaction allows the atom‐economic and efficient formation of valuable α‐amino acid derivatives (see scheme); the key step is an intramolecular stereoselective protonation. For the first time, a β‐unsu...