A complementary method to obtain N-acyl enamides using the Heck reaction: Extending the substrate scope for asymmetric hydrogenation

Tetrahedron Letters

Volumn 45, Issue 50, 2004, Pages 9277-9280

  Harrison, Paul ^a   Meek, Graham ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

Asymmetric hydrogenation; Heck reaction; N Acyl enamides

Indexed keywords

ACETAMIDE DERIVATIVE; AMIDE; AMINE; SULFONIC ACID DERIVATIVE;

ANALYTIC METHOD; ARTICLE; COMPLEX FORMATION; DEACYLATION; ENANTIOSELECTIVITY; HECK REACTION; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 8544242698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.063     Document Type: Article

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16. 1H NMR δ (400 MHz, DMSO) 8.41 (2H, br s), 7.68 (1H, s), 7.56 (1H, d, J 8 Hz), 7.35 (1H, d, J 8 Hz), 4.28 (1H, q, J 6 Hz) and 1.32 (3H, d, J 6 Hz). 2·HCl (4 mg) was dissolved in MTBE (2 mL) and washed with 2 M NaOH (2 mL). GC analysis of the MTBE solution indicated >98% ee (Chirasil Dex-CB, Helium (20 psi), 100°C for 30 min ramped to 200°C at 5°C/min, (S)-2·HCl: 40.5 min, (R)-2·HCl: 40.4 min)