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Volumn 6, Issue 5, 2000, Pages 906-913

Enantioselective Diels - Alder approach to C-3-oxygenated angucyclinones from (SS)-2-(p-tolylsulfinyl)-1,4-naphthoquinone

Author keywords

Angucyclinones; Asymmetric synthesis; Cycloadditions; Kinetic resolution; Sulfinylquinones

Indexed keywords

1,4 NAPHTHOQUINONE; ANGUCYCLINE DERIVATIVE; ANGUCYCLINONE DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; NAPHTHOQUINONE; UNCLASSIFIED DRUG;

EID: 0034599077     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000303)6:5<906::aid-chem906>3.0.co;2-g     Document Type: Article
Times cited : (45)

References (53)
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    • note
    • For the sake of clarity, the numbering used for carbinols 2a and 2d was the same as the ones of the corresponding ethers. [18] L. N. Mander, S. P. Sethi, Tetrahedron Lett. 1984, 25, 5953-5956.
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    • note
    • The nomenclature anti is used for adducts that result when the dienophile approaches the face of the diene opposite to the OX function in the initial cycloaddition. The syn adducts result from the approach onto the face bearing the OX substituent.
  • 40
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    • note
    • 1H NMR spectra of racemic samples in the presence of different chiral lanthanide shift reagents of Eu, Pr and Yb were not well-defined and separate.
  • 41
    • 85088333276 scopus 로고    scopus 로고
    • note
    • 12b did not appear as a well-resolved signal, and for 6b and 6c this proton overlapped with the hydrogens at C-6 (see Experimental Section).
  • 42
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    • note
    • 6 at 500 MHz.
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    • We use this term in the conventional sense, as defined by Masamune et al. (see S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-31), the kinetically favored reaction is considered to be the one occurring between homochiral dienophile (+)-1 and one of the enantiomers of chiral racemic dienes 2.
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  • 44
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    • We use this term in the conventional sense, as defined by Masamune et al. (see S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-31), the kinetically favored reaction is considered to be the one occurring between homochiral dienophile (+)-1 and one of the enantiomers of chiral racemic dienes 2.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 1-31
  • 45
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    • note
    • The same S configuration is always produced by a chiral (SS)-2-(p-tolylsulfinyl)-1,4-quinone upon reaction with (1E)-substituted dienes (see refs. [10b, 10e] and [13]).
  • 48
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    • note
    • -1 in cyclohexane derivatives: see ref. [25], p. 697.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.