NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (-)-cytoxazone and droxidopa

Tetrahedron Letters

Volumn 48, Issue 8, 2007, Pages 1375-1378

  George, Shyla ^a   Narina, Srinivasarao V ^a   Sudalai, Arumugam ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Asymmetric bromohydroxylation; Carboxamide; Cytoxazone; Droxidopa; NaIO4

Indexed keywords

ALPHA BROMO BETA HYDROXYCARBOXAMIDE; AMIDE; CYTOXAZONE; PERIODATE SODIUM; THREO 3,4 DIHYDROXYPHENYLSERINE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BIOLOGICAL ACTIVITY; DRUG HYDROXYLATION; DRUG MECHANISM; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 33846345656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.109     Document Type: Article

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38. 4 and concentrated under reduced pressure to give the crude bromohydrin products, which were then purified by column chromatography on silica gel (60-120 mesh) eluting with petroleum ether and ethyl acetate (7:3) to afford pure products 2 and 3.
39. 6 requires C, 64.29; H, 4.90; Br, 12.96; N, 2.27. Found: C, 64.01; H, 5.21; Br, 12.69; N, 2.49.