Highly enantioselective organocatalytic addition of unmodified aldehydes to N-Boc protected imines: one-pot asymmetric synthesis of β-amino acids

Tetrahedron Letters

Volumn 48, Issue 3, 2007, Pages 421-425

  Vesely, Jan ^a   Rios, Ramon ^a   Ibrahem, Ismail ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALCOHOL; BETA AMINO ACID; IMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DEPROTECTION REACTION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MANNICH REACTION; ONE POT SYNTHESIS; OXIDATION REDUCTION REACTION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33845414246     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.076     Document Type: Article

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76. The reaction also works for Cbz protected alimines. For instance, the reaction between benzaldehyde derived Cbz protected imine (0.25 mmol) and propionaldehyde (0.5 mmol) in DMF at 4 °C gave the corresponding Cbz protected β-aminoaldehyde after 17 h in 80% yield with 4:1 dr and 72% ee.