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Volumn 128, Issue 19, 2006, Pages 6499-6507

Tandem nucleophilic addition/fragmentation reactions and synthetic versatility of vinylogous acyl triflates

Author keywords

[No Author keywords available]

Indexed keywords

FRAGMENTATION REACTIONS; GRIGNARD REAGENTS; NUCLEOPHILES; TANDEM NUCLEOPHILIC ADDITION; VINYLOGOUS ACYL TRIFLATES;

EID: 33646548297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0608085     Document Type: Article
Times cited : (71)

References (76)
  • 2
    • 0000851696 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (b) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 133-238.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133-238
    • Heathcock, C.H.1
  • 4
    • 0001546712 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (b) Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 551-592.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 551-592
    • Sweger, R.W.1    Czarnik, A.W.2
  • 6
    • 0003148146 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 1-67.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1-67
    • Jung, M.E.1
  • 7
    • 0000746177 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (a) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 785-826.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 785-826
    • Hill, R.K.1
  • 8
    • 33845471185 scopus 로고
    • (b) Lutz, R. P. Chem. Rev. 1984, 84, 205-247.
    • (1984) Chem. Rev. , vol.84 , pp. 205-247
    • Lutz, R.P.1
  • 9
    • 0000036757 scopus 로고
    • Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford
    • Lee, D. G.; Chen, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 541-591.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 541-591
    • Lee, D.G.1    Chen, T.2
  • 10
    • 0000814530 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • Shing, T. K. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford. 1991; Vol. 7. pp 703-717.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 703-717
    • Shing, T.K.M.1
  • 11
    • 0001373505 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • Hudlicky, T.; Reed, J. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899-970.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899-970
    • Hudlicky, T.1    Reed, J.E.2
  • 12
    • 11844273927 scopus 로고    scopus 로고
    • For reviews, see: (a) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610 and references therein.
    • (2004) Chem. Soc. Rev. , vol.33 , pp. 610
    • Jun, C.-H.1
  • 16
    • 1442360753 scopus 로고    scopus 로고
    • Grubbs, R. H., Ed.; Wiley-VCH: Weinheim
    • (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
    • (2003) Handbook of Metathesis
  • 27
    • 0000873998 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For other reviews on the Grob-type fragmentations, see: (a) Weyerstahl, P.; Marschall, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6. pp 1041-1070.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 1041-1070
    • Weyerstahl, P.1    Marschall, H.2
  • 29
    • 15444380646 scopus 로고    scopus 로고
    • For selected applications of the Eschenmoser-Tanabe fragmentation in total synthesis, see: (a) Murakami, Y.; Shindo, M.; Shishido, K. Synlett 2005, 664.
    • (2005) Synlett , pp. 664
    • Murakami, Y.1    Shindo, M.2    Shishido, K.3
  • 47
    • 33646578687 scopus 로고    scopus 로고
    • note
    • Impurities in aged stock solutions of n-BuLi, such as LiOH and n-BuOLi, may cause decomposition of 1a or may alter the aggregation properties of the nucleophile. TMEDA seemed to abrogate this effect.
  • 50
    • 0007881676 scopus 로고
    • Reactions of (trimethylsilyl)methyllithium with enol ethers of 1,3-cyclohexanedione derivatives have been reported, see: (a) Horiguchi, Y.; Kataoka, Y.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 3327.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3327
    • Horiguchi, Y.1    Kataoka, Y.2    Kuwajima, I.3
  • 53
    • 33646540938 scopus 로고    scopus 로고
    • note
    • 3Si group occurred during purification.
  • 58
    • 0000010274 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For reviews on the Claisen condensation, see: (a) Davis, B. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2. pp 795-863.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 795-863
    • Davis, B.R.1    Garratt, P.J.2
  • 62
    • 33646572760 scopus 로고    scopus 로고
    • note
    • 3. See Supporting Information for details.
  • 63
    • 33646581588 scopus 로고    scopus 로고
    • note
    • + = 261.1); however, the yield was quite low, and we could not isolate the desired product in acceptable purity. In the latter case, the reaction resulted in the decomposition of triflate 1a, and a significant amount of ethyl isobutyrate was recovered.
  • 64
    • 33646541583 scopus 로고    scopus 로고
    • note
    • A further mechanistic discussion can be found in our earlier paper; see ref 19.
  • 72
    • 0003703778 scopus 로고    scopus 로고
    • Czarnik, A. W., DeWitt, S. H.; Eds.; American Chemical Society: Washington, DC
    • For reviews on combinatorial chemistry, see: (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
  • 75
    • 33646586271 scopus 로고    scopus 로고
    • note
    • 1H NMR data consistent with metastable intermediate C1′ were routinely observed during spectroscopic analysis of the crude reaction mixtures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.