Substrate-directed stereoselectivity in vicinal diamine-catalyzed synthesis of warfarin

Organic Letters

Volumn 8, Issue 23, 2006, Pages 5239-5242

  Kim, Hyunwoo ^a   Yen, Cindy ^a   Preston, Philippa ^a   Chin, Jik ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845262220     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062000v     Document Type: Article

References (38)

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35. 1H NMR (Supporting Information).
36. It may be that the rate-determining step for 6-catalyzed synthesis of warfarin is the imine formation step and is acid catalyzed. In contrast, it appears that for 5-catalyzed synthesis of warfarin, the imine formation step is fast and not rate determining. Background reaction involving direct addition of 2 to 3 should lower the stereoselectivity. Acetic acid is expected to increase the stereoselectivity by facilitating and activating the diimine pathway.
37. Density functional theory (DFT) calculation was performed using Spartan '04 Windows from Wavefunction, Inc. NCCN dihedral angles were obtained by molecular mechanics computation using the same software.
38. 2 = 1.019.