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Volumn 127, Issue 23, 2005, Pages 8260-8261

An anomeric control on remote stereochemistry in the synthesis of spiroketals

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; OXYGEN; PYRAN; SPIROKETAL; UNCLASSIFIED DRUG;

EID: 20444477462     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051745d     Document Type: Article
Times cited : (31)

References (30)
  • 3
    • 0004231915 scopus 로고
    • CRC Press: Ann Arbor, MI
    • For reviews on anomeric effect related to carbohydrate chemistry, see: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Ann Arbor, MI, 1995.
    • (1995) C-Glycoside Synthesis
    • Postema, M.H.D.1
  • 5
    • 3042828434 scopus 로고    scopus 로고
    • For some elegant studies on anomeric effects, see: (a) Smith, D. M.; Woerpel, K. A. Org. Lett. 2004, 6, 2063.
    • (2004) Org. Lett. , vol.6 , pp. 2063
    • Smith, D.M.1    Woerpel, K.A.2
  • 23
    • 20444494666 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details of characterizations.
  • 24
    • 20444491307 scopus 로고    scopus 로고
    • note
    • The other six possible conformations would lose either one of the two or both anomerically favored axial oxygen substituents, although some of them can still lead to the observed relative stereochemistry at C2-3.
  • 25
    • 20444495417 scopus 로고    scopus 로고
    • note
    • It is noteworthy that the elimination product dienone 10 was not found when reactions are run at lower concentrations. This helped providing a more distinct cis:trans ratio. However, dienone 10 is only a real minor product even at concentrations higher than 0.05 M.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.