A Novel Ring-Enlargement Reaction of (3-Oxa-2-silacyclopentyl)methyl Radicals into 4-Oxa-3-silacyclohexyl Radicals. Stereoselective Introduction of a Hydroxyethyl Group via Unusual 6-Endo-Cyclization Products Derived from 3-Oxa-4-silahexenyl Radicals and Its Application to the Synthesis of a 4′-α-Branched Nucleoside

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5676-5677

  Shuto, Satoshi ^a   Kanazaki, Makiko ^a   Ichikawa, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; NUCLEOSIDE DERIVATIVE; RADICAL; SILANE DERIVATIVE; SILICON DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030850585     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970867o     Document Type: Article

References (55)

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44. Although the reaction pathway of the radical B to C is unclear, two intermediates may be postulated: as shown below, (1) a fragmentation intermediate and (2) an intermediate assisted by a bridging interaction between silicon and the unpaired electron of the β-silyl radical [this kind of bridging interaction has been suggested through both kinetic studies (Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207-208), and MO calculation (Pitt, C. G. J. Organomet. Chem. 1973, 61, 49.)]. equation presented
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47. Known 1,2- rearrangement of carbon-centered radicals: (a) Wilt, J. W.; Pawlikowski, W. W., Jr. J. Org. Chem. 1975, 40, 3641. (b) Goermer, R. N.; Cote, P. N., Jr.; Vittimberga, B. M. J. Org. Chem. 1977, 42, 19. (c) Stork, G.; Mook Jr., R. J. Am. Chem. Soc. 1987, 109, 2829. (d) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565. (e) Dowd, P.; Ahang, W. Chem. Rev. 1993, 93, 2091.
48. Known 1,2- rearrangement of carbon-centered radicals: (a) Wilt, J. W.; Pawlikowski, W. W., Jr. J. Org. Chem. 1975, 40, 3641. (b) Goermer, R. N.; Cote, P. N., Jr.; Vittimberga, B. M. J. Org. Chem. 1977, 42, 19. (c) Stork, G.; Mook Jr., R. J. Am. Chem. Soc. 1987, 109, 2829. (d) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565. (e) Dowd, P.; Ahang, W. Chem. Rev. 1993, 93, 2091.
49. Known 1,2- rearrangement of carbon-centered radicals: (a) Wilt, J. W.; Pawlikowski, W. W., Jr. J. Org. Chem. 1975, 40, 3641. (b) Goermer, R. N.; Cote, P. N., Jr.; Vittimberga, B. M. J. Org. Chem. 1977, 42, 19. (c) Stork, G.; Mook Jr., R. J. Am. Chem. Soc. 1987, 109, 2829. (d) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565. (e) Dowd, P.; Ahang, W. Chem. Rev. 1993, 93, 2091.
50. A gas phase 1,2-migration of trimethylsilyl group in an aromatic β-silyl biradical has been reported: Johnson, G. C.; Stofko, J. J., Jr.; Lockhart, T. P.; Brown, D. W.; Bergman, R. G. J. Org. Chem. 1979, 44, 4215.
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52. Carbon to oxygen or to nitrogen 1,2-silicon migrations in oxygenor nitrogen-centered β-silyl radicals have been known: (a) Harris, J. M.; MacInnes, I.; Walton, J. C.; Maillard, B. J. Organometal. Chem. 1991, 403, C25. (b) Tsai, Y.-M.; Cherng, C.-D. Tetrahedron Lett. 1991, 32, 3515.
53. An intramolecular homolytic substituent of δ-silyl carboncentered radicals at the silicon in liquid phase has been reported: Kulicle, K. J.; Chatgiliatoglu, C.; Kopping, B.; Giese, B. Helv. Chim. Acta 1992, 75, 935.
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55. The stereochemistry of 1 was determined by NOE experiments.