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Volumn 71, Issue 6, 2006, Pages 2257-2266

Spacer-mediated synthesis of contra-thermodynamic spiroacetals: Stereoselective synthesis of C2-symmetric difructose dianhydrides

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC ISOPROPYLIDENE FRUCTOSE DERIVATIVES; BIS-SPIROACETAL DERIVATIVES; CONTRA-THERMODYNAMIC SPIROACETALS; CONTRATHERMODYNAMIC DIFRUCTOFURANOSE; DIFRUCTOSE DIANHYDRIDES; SPIROKETAL CENTERS; STEREOSELECTIVE SYNTHESIS; SYMMETRIC DIFRUCTOSE DIANHYDRIDES; XYLYLENE MOIETY;

EID: 33645024481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052184b     Document Type: Article
Times cited : (17)

References (57)
  • 21
    • 12944312239 scopus 로고    scopus 로고
    • The term "contra-thermodynamic" designates diastereomers that are energetically strongly disfavored and, consequently, cannot be access under reversible kinetics or thermodynamic conditions. For remarkable recent examples of stereoselective syntheses of contra-thermodynamic spiroacetal frameworks, see: (a) Takaoka, L. R.; Buckmelter, A. J.; LaCruz, T. E.; Rychnovsky, S. D. J. Am. Chem. Soc. 2005, 127, 528-529.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 528-529
    • Takaoka, L.R.1    Buckmelter, A.J.2    Lacruz, T.E.3    Rychnovsky, S.D.4
  • 43
    • 0038418607 scopus 로고    scopus 로고
    • The rigid spacer concept has been previously exploited in anomeric configuration control during glycosidic bond-forming reactions. See: (a) Müller, M.; Huchel, U.; Geyer, A.; Schmidt, R.-R. J. Org. Chem. 1999, 64, 6190-6201.
    • (1999) J. Org. Chem. , vol.64 , pp. 6190-6201
    • Müller, M.1    Huchel, U.2    Geyer, A.3    Schmidt, R.-R.4
  • 55
    • 20444477462 scopus 로고    scopus 로고
    • An example of remote stereochemical control in the stereoselective synthesis of spiroketals by a preexisting cyclic acetal functionality has recently been reported. See: Ghosh, S.; Hsung, R. P.; Liu, J. J. Am. Chem. Soc. 2005, 127, 8260-8261.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 8260-8261
    • Ghosh, S.1    Hsung, R.P.2    Liu, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.