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Volumn 7, Issue 8, 1996, Pages 2303-2312

The influence of electronic effects and temperature on the enantioselective reductions of acetophenone derivatives with (-)-diisopinocampheylchloroborane - A dynamic model of enantioselection

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE;

EID: 0030221454     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00285-6     Document Type: Article
Times cited : (10)

References (27)
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  • 5
    • 0001431355 scopus 로고    scopus 로고
    • 4 Recently, a very interesting semiempirical study and conformational analysis of asymmetric reductions with Alpine Borane™ has been published: M.M. Rogic, J. Org. Chem. 1996, 61, 1341-6
    • (1996) J. Org. Chem. , vol.61 , pp. 1341-1346
    • Rogic, M.M.1
  • 11
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    • b) H. Buschmann, H.-D. Scharf, N. Hoffmann, P. Esser, Angew. Chem. 1991, 103, 480-518, Angew. Chem. Int. Ed. Engl. 1991, 30, 477-515.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 477-515
  • 14
    • 85030271291 scopus 로고    scopus 로고
    • inv corresponds to a temperature not tolerated by the reaction (temperature window) or the reaction proceeds via a mechanism, which furnishes selectivity in only one step (e.g. in concerted reactions)
    • inv corresponds to a temperature not tolerated by the reaction (temperature window) or the reaction proceeds via a mechanism, which furnishes selectivity in only one step (e.g. in concerted reactions).
  • 15
    • 0001050315 scopus 로고
    • 10. T. Göbel, K.B. Sharpless, Angew. Chem. 1993, 105, 1417-8; Angew. Chem. Int. Ed. Engl. 1993, 32, 1339-41.
    • (1993) Angew. Chem. , vol.105 , pp. 1417-1418
    • Göbel, T.1    Sharpless, K.B.2
  • 16
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    • 10. T. Göbel, K.B. Sharpless, Angew. Chem. 1993, 105, 1417-8; Angew. Chem. Int. Ed. Engl. 1993, 32, 1339-41.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1339-1341
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    • 11 G. Erker, T. Fritze, Angew. Chem. 1992, 104, 204-6; Angew. Chem. Int. Ed. Engl. 1992, 31, 199-201.
    • (1992) Angew. Chem. , vol.104 , pp. 204-206
    • Erker, G.1    Fritze, T.2
  • 18
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    • 11 G. Erker, T. Fritze, Angew. Chem. 1992, 104, 204-6; Angew. Chem. Int. Ed. Engl. 1992, 31, 199-201.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 199-201
  • 23
    • 85030276470 scopus 로고    scopus 로고
    • This is advisable, as with the used permethylated cyclodextrin phase, the underivatised phenylethanols show significant tailings. This often makes baseline separations impossible, thus diminishing the accuracy of enantiomer analysis. This drawback is avoided by derivatising the alcohol
    • 16. This is advisable, as with the used permethylated cyclodextrin phase, the underivatised phenylethanols show significant tailings. This often makes baseline separations impossible, thus diminishing the accuracy of enantiomer analysis. This drawback is avoided by derivatising the alcohol.
  • 24
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    • note
    • 1 have shown, that no such reaction occurs even at 25 °C, a second equivalent of α-pinene could theoretically be eliminated at elevated temperatures. We checked this in an experiment, where 2 eq. of acetophenone reacted with 1 eq. of 1 at +64 °C under standard conditions. We found that only 1 eq. acetophenone was consumed in this reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.