메뉴 건너뛰기




Volumn 127, Issue 14, 2005, Pages 5028-5029

A tandem carbanion addition/carbon-carbon bond cleavage yields alkynyl ketones

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALKYNYL GROUP; CARBON; CARBOXYLIC ACID DERIVATIVE; CYCLOALKENE; KETONE DERIVATIVE; METHANOL; TOLUENE;

EID: 17144392896     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050663m     Document Type: Article
Times cited : (60)

References (31)
  • 1
    • 0000036757 scopus 로고
    • Cleavage reactions
    • Trost, B. M., Fleming, T., Eds.; Pergamon Press: Elmsford, NY
    • Lee, D. G.; Chen, T. Cleavage Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, T., Eds.; Pergamon Press: Elmsford, NY, 1991; Vol. 7, p 541.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 541
    • Lee, D.G.1    Chen, T.2
  • 2
    • 0000746177 scopus 로고
    • Cope, oxy-cope and anionic oxy-cope rearrangements
    • Trost. B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY
    • Hill, R. K. Cope, Oxy-Cope and Anionic Oxy-Cope Rearrangements. In Comprehensive Organic Synthesis; Trost. B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; Vol. 5, p 785.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 785
    • Hill, R.K.1
  • 3
  • 8
    • 0000873998 scopus 로고
    • Fragmentation reactions
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY
    • (a) Weyerstahl, P.; Marschall, H. Fragmentation Reactions. Tn Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; Vol. 6, pp 1041-1070.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 1041-1070
    • Weyerstahl, P.1    Marschall, H.2
  • 16
    • 0342768006 scopus 로고
    • 2Ph, prepared in three steps from 5c) fragment upon subsequent treatment with base (i.e., NaH): Shimizu, M.; Ando, R.; Kuwajima, I. J. Org. Chem. 1981, 46, 5246.
    • (1981) J. Org. Chem. , vol.46 , pp. 5246
    • Shimizu, M.1    Ando, R.2    Kuwajima, I.3
  • 17
    • 0003703778 scopus 로고    scopus 로고
    • Czarnik, A. W., DeWitt, S. H., Eds.; American Chemical Society: Washington, DC
    • (a) A Practical Guide to Combinatorial Chemistry; Czarnik, A. W., DeWitt, S. H., Eds.; American Chemical Society: Washington, DC, 1997.
    • (1997) A Practical Guide to Combinatorial Chemistry
  • 19
    • 17144362286 scopus 로고    scopus 로고
    • note
    • (a) See Supporting Information for details,
  • 21
    • 17144424760 scopus 로고    scopus 로고
    • note
    • We postulate a late transition state with significant carbonyl character.
  • 22
    • 0008183432 scopus 로고
    • Compound 8g has also been synthesized by the Eschenmoser-Tanabe strategy in four steps (32% overall): Harding, C. E.; King, S. L. J. Org. Chem. 1992, 57, 883.
    • (1992) J. Org. Chem. , vol.57 , pp. 883
    • Harding, C.E.1    King, S.L.2
  • 27
    • 17144388387 scopus 로고
    • (a) Harada, R. Nippon Kagaku Zasshi 1956, 77, 990; Chem. Abstr. 1957, 51, 18489.
    • (1957) Chem. Abstr. , vol.51 , pp. 18489
  • 29
    • 17144411284 scopus 로고
    • (b) Harada, R. Nippon Kagaku Zasshi 1956, 77, 1036; Chem. Abstr. 1959, 53, 21773.
    • (1959) Chem. Abstr. , vol.53 , pp. 21773
  • 31
    • 17144415365 scopus 로고    scopus 로고
    • note
    • Nonconcerted fragmentation pathways should also be considered. We thank a referee for pointing this out.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.