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Volumn 124, Issue 48, 2002, Pages 14306-14307

Novel radical alkylation of carboxylic imides

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE; RADICAL;

EID: 0037021565     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028396x     Document Type: Article
Times cited : (34)

References (34)
  • 1
    • 0003592858 scopus 로고
    • Benjamin W. A., Menlo Park, CA, Chapter 9
    • (a) House, H. O. Modern Synthetic Reactions; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 9.
    • (1972) Modern Synthetic Reactions
    • House, H.O.1
  • 2
    • 0002782655 scopus 로고
    • Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: Oxford
    • (b) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 1-63.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 1-63
    • Caine, D.1
  • 4
    • 0001216647 scopus 로고
    • Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford
    • (a) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 715-831.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 715-831
    • Curran, D.P.1
  • 5
    • 0004269715 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • (b) Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2.
    • (2001) Radicals in Organic Synthesis , vol.1-2
  • 25
    • 0011819570 scopus 로고    scopus 로고
    • note
    • 2) which were somewhat less stable than 1a and 1b.
  • 26
    • 0030878188 scopus 로고    scopus 로고
    • When lithium enolate of 6 was quenched with TBSOTf at -78°C, 5 was isolated in 40% yield. Thus, it is essential to generate lithium enolate of 6 in the presence of TBSOTf and diethyl chlorophosphate to yield 1a and 1b. (a) Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gartner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467. (b) Jiang, J.; DeVita, R. J.; Doss, G. A.; Goulet, M. T.; Wyvratt, M. J. J. Am. Chem. Soc. 1999, 121, 593.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5467
    • Nicolaou, K.C.1    Shi, G.-Q.2    Gunzner, J.L.3    Gartner, P.4    Yang, Z.5
  • 27
    • 0033608115 scopus 로고    scopus 로고
    • When lithium enolate of 6 was quenched with TBSOTf at -78°C, 5 was isolated in 40% yield. Thus, it is essential to generate lithium enolate of 6 in the presence of TBSOTf and diethyl chlorophosphate to yield 1a and 1b. (a) Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gartner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467. (b) Jiang, J.; DeVita, R. J.; Doss, G. A.; Goulet, M. T.; Wyvratt, M. J. J. Am. Chem. Soc. 1999, 121, 593.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 593
    • Jiang, J.1    DeVita, R.J.2    Doss, G.A.3    Goulet, M.T.4    Wyvratt, M.J.5
  • 32
    • 0011861872 scopus 로고    scopus 로고
    • note
    • Since the rate of addition of a nucleophilic alkyl radical onto 1 would be relatively slow, the alkyl radical might react with a silyloxy radical, thereby stopping the radical chain reaction.
  • 33
    • 0011825399 scopus 로고    scopus 로고
    • note
    • 2 (1.0 equiv) was almost completely consumed during the reaction. The structures of 9 and 10 are tentatively assigned.
  • 34
    • 0011820165 scopus 로고    scopus 로고
    • note
    • 2 in benzene at 300 nm for 6 h gave 4,4′-bromodibenzyl in 80% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.