3-Fluoro-6-tert-butyltetrahydropyranosyl trichloroacetamidates. "Chiral auxiliary donors" for hydroxyalkyl radicals

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1217-1219

  Garner, Philip ^a   Şeşenoǧlu, Özge ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ACRYLIC ACID DERIVATIVE; ALKYL GROUP; FLUORINE DERIVATIVE; HYDROXYL RADICAL; METHYL 2 TRIFLUOROACETOXYACRYLATE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; GLYCOSYLATION; METHODOLOGY; PRECURSOR;

ALKANES; CYCLIZATION; FLUORINE; GLYCOSYLATION; HYDROXYL RADICAL; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM; TRICHLOROACETIC ACID;

EID: 2542443380     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049922n     Document Type: Article

References (14)

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4. 2 nucleus. See: Fried, J.; Hallinan, E. A.; Szwedo, M. J. J. Am. Chem. Soc. 1984, 106, 3871.
5. We recently reported a camphor-derived chiral auxiliary for hydroxyalkyl radicals that also incorporated an analogous fluorinated THP unit into its structure. However, the diastereofacial selectivity observed with this auxiliary was only modest (ds ≤ 4.5:1 at -78°C) due to geometrically induced distortion of the THP ring from an ideal chair conformation. See: Garner, P.; Sesenoglu, O.; Burgoon, H. Tetrahedron: Asymmetry 2003, 14, 2883.
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14. In every system that we have examined thus far, the diastereotopic methylene protons α to the ketone in the major diastereomer resonate upfield of the corresponding signals of the minor diastereomer (see the Supporting Information for details.)