Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OiPr)3/amide-based ligand catalyst

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2140-2143

  Takechi, Sho ^a,b   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Amide based ligand; Asymmetric catalysis; Asymmetric hydroxylation; Rare earth metal; Tetrasubstituted stereogenic centers

Indexed keywords

ALPHA ALKOXYCARBONYL AMIDE; AMIDE; LIGAND; NUCLEOPHILE; OXAZIRIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; COORDINATION; DRUG HYDROXYLATION; HYDROGEN BOND; HYDROXYLATION;

EID: 79953168364     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.064     Document Type: Article

References (43)

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38. The absolute configuration of other products was deduced by analogy.
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40. At this stage, the absolute of the product 4j obtained from aliphatic substrate 1j with oxaziridine 6 is uncertain. The isolation of the product 4j required iterative chromatography.
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42. 3/(S)-2a (La: (S)-2a = 1:2) catalyst (10 mol %) in DMF solvent (0.2 M) delivered 4a in 24% yield, 5% ee, which is significantly poor result compared with that of entry 2 in Table 1.
43. See Supplementary data for details.