Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses

Organic Letters

Volumn 4, Issue 10, 2002, Pages 1771-1774

  Haukaas, Michael H ^a   O'Doherty, George A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIDEOXYHEXOSE; 2,3-DIDEOXYHEXOSE; AMINOGLYCOSIDE; ANTIINFECTIVE AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HEXOSE; MONOSACCHARIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; HEXOSES; INDICATORS AND REAGENTS; MONOSACCHARIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037118313     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025844x     Document Type: Article

References (31)

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16. The enantioselectivity was increased to >98% after recrystallization of the furan diol bisbenzoate.
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21. These model studies were carried out on the anomeric pivolate because of the propensity of allylic esters to undergo hydrogenolysis reactions. Thus a procedure established on this substrate should have the greatest substrate generality.
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23. Prepared by the method of Heck: Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083. Also see: Pasto, D. J. Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: 1991; Vol. 40, p 91.
24. Prepared by the method of Heck: Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083. Also see: Pasto, D. J. Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: 1991; Vol. 40, p 91.
25. 1H NMR, it was easily converted to product by re-subjecting the crude product to the reaction conditions.
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31. We have already shown that the allylic alcohols 9 and 10 are ideal substrates for the Mitsunobu reaction; see refs 9 and 11.