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Volumn 122, Issue 39, 2000, Pages 9386-9390

Conformational memory in enantioselective radical reductions and a new radical clock reaction

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; RADICAL; TETRAHYDROPYRAN DERIVATIVE;

EID: 0034605472     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002068k     Document Type: Article
Times cited : (57)

References (44)
  • 22
    • 0003942864 scopus 로고
    • John Wiley & Sons: New York
    • Cyclohexane and tetrahydropyran have ring-inversion barriers of about 10 kcal/mol, but the cydohexyl radical has a ring-inversion barrier of only 5.5 kcal/mol. (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 740-742. (b) Roberts, B. P.; Steel, A. J. J. Chem. Soc., Perkin Trans. 2 1992, 2025- 2029.
    • (1994) Stereochemistry of Organic Compounds , pp. 740-742
    • Eliel, E.L.1    Wilen, S.H.2
  • 23
    • 37049070157 scopus 로고
    • Cyclohexane and tetrahydropyran have ring-inversion barriers of about 10 kcal/mol, but the cydohexyl radical has a ring-inversion barrier of only 5.5 kcal/mol. (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 740-742. (b) Roberts, B. P.; Steel, A. J. J. Chem. Soc., Perkin Trans. 2 1992, 2025-2029.
    • (1992) J. Chem. Soc., Perkin Trans. 2 , pp. 2025-2029
    • Roberts, B.P.1    Steel, A.J.2
  • 24
    • 0342663467 scopus 로고    scopus 로고
    • Details for the preparation and resolution of 1 are provided in the Supporting Information
    • Details for the preparation and resolution of 1 are provided in the Supporting Information.
  • 28
    • 0343097764 scopus 로고
    • Ph.D. Thesis, University of Minnesota
    • (a) Skalitzky, D. Ph.D. Thesis, University of Minnesota, 1992.
    • (1992)
    • Skalitzky, D.1
  • 34
    • 0343533734 scopus 로고    scopus 로고
    • note
    • R[RSH].
  • 36
    • 0343097763 scopus 로고    scopus 로고
    • note
    • 6. The standard deviation was smaller for reactions run simultaneously in the same cooling bath, suggesting that some of the scatter can be attributed to imprecise temperature control.
  • 38
  • 40
    • 0343097761 scopus 로고    scopus 로고
    • This assumes that the trapping agents are achiral. Chiral trapping agents would lead to diastereomeric transition states. However, most trapping agent of interest are achiral
    • This assumes that the trapping agents are achiral. Chiral trapping agents would lead to diastereomeric transition states. However, most trapping agent of interest are achiral.
  • 42
    • 0342663466 scopus 로고    scopus 로고
    • tMS) = (9.26 ± 0.13) - (1.78 ± 0.26)/2.3RT. See ref 21
    • tMS) = (9.26 ± 0.13) - (1.78 ± 0.26)/2.3RT. See ref 21.
  • 44
    • 0343097762 scopus 로고    scopus 로고
    • The general experimental section is included in the Supporting Information
    • The general experimental section is included in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.