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Volumn 67, Issue 21, 2002, Pages 7439-7445

Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR GLYCOSIDATION;

EID: 0037131158     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026004z     Document Type: Article
Times cited : (77)

References (65)
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    • note
    • 3 as implemented in version 7.0 of the MacroModel and BatchMin packages.
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    • 2 system has been used for the deprotection of carbohydrate benzyl ethers in the presence of a suitably located hydroxyl group. We have not detected debenzylation or formation of benzylidene to an appreciable extent in this case (Madsen, J.; Viuf, C.; Bols, M. Chem. Eur. J. 2000, 6, 1140-1146).
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    • For studies on stereoelectronic effects in intermolecular hydrogen abstraction reactions see: (a) Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
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    • Malatesta, V.1    Ingold, K.U.2
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    • For studies on stereoelectronic effects in intermolecular hydrogen abstraction reactions see: (a) Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609-614. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
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    • (2002) Org. Lett. , vol.4 , pp. 1959-1961
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    • For the use of this methodology with carbohydrates possessing sensitive protecting groups see: (a) Gonzále, C. C.; Kennedy, A. R.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. Angew. Chem., Int. Ed. 2001, 40, 2326-2328. (b) Francisco, C. G.; Freire, R.; González, C. C.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. J. Org. Chem. 2001, 66, 1861-1866. (c) Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2326-2328
    • Gonzále, C.C.1    Kennedy, A.R.2    León, E.I.3    Riesco-Fagundo, C.4    Suárez, E.5
  • 64
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    • For the use of this methodology with carbohydrates possessing sensitive protecting groups see: (a) Gonzále, C. C.; Kennedy, A. R.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. Angew. Chem., Int. Ed. 2001, 40, 2326-2328. (b) Francisco, C. G.; Freire, R.; González, C. C.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. J. Org. Chem. 2001, 66, 1861-1866. (c) Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866.
    • (2001) J. Org. Chem. , vol.66 , pp. 1861-1866
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    • For the use of this methodology with carbohydrates possessing sensitive protecting groups see: (a) Gonzále, C. C.; Kennedy, A. R.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. Angew. Chem., Int. Ed. 2001, 40, 2326-2328. (b) Francisco, C. G.; Freire, R.; González, C. C.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. J. Org. Chem. 2001, 66, 1861-1866. (c) Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8865-8866
    • Armas, P.1    Francisco, C.G.2    Suárez, E.3


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