Dynamic kinetic resolution of hemiaminals using a novel DMAP catalyst

Tetrahedron Letters

Volumn 49, Issue 1, 2008, Pages 32-35

  Yamada, Shinji ^a   Yamashita, Kaori ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINOPYRIDINE DERIVATIVE; DIMETHYLAMINOPYRIDINE; ESTER; HEMIAMINAL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; DYNAMIC KINETIC RESOLUTION; TEMPERATURE;

GOSSYPIUM HIRSUTUM;

EID: 36549049271     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.026     Document Type: Article

References (22)

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16. 3N (21 μL) and isobutyric anhydride (25 μL) at 0 °C. The solution was stirred for 8 h at rt. MeOH was added to the reaction mixture, and the solution was stirred for 20 min. The reaction mixture was concentrated and the residue was purified by preparative TLC (hexane/AcOEt = 4/1) to give the product ester 8c (40.0 mg). The enantiomeric excess of the ester was determined by HPLC analysis using Daicel CHIRALPAK AD column using 9:1 mixture of hexane and i-PrOH as an eluent solvent.
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20. 2 are 0.0365 [I > 2σ(I)] and 0.1050 (all data), respectively. CCDC 661154.
21. The distance between the hydrogen atom of HO(1) and O(3) atom is ca. 2.6 Å and that for O(1) and O(3) is 2.998 Å which is within a range of general O-H⋯O hydrogen bond.
22. * level by using Spartan 06'. The calculations predicted only one stable conformer in which two carbonyl groups have an opposite direction with a hydrogen bonding between the hydroxy group and the carbonyl group.