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Volumn 9, Issue 13, 2007, Pages 2581-2584

N-heterocyclic carbene-initiated α-acylvinyl anion reactivity: Additions of α-hydroxypropargylsilanes to aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HETEROCYCLIC COMPOUND; SILANE DERIVATIVE;

EID: 34547219364     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0710515     Document Type: Article
Times cited : (46)

References (60)
  • 1
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    • For a review of the MBH reaction, see:, For mechanistic studies
    • For a review of the MBH reaction, see: Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891. For mechanistic studies,
    • (2003) Chem. Rev , vol.103 , pp. 811-891
    • Basavaiah, D.1    Rao, A.J.2    Satyanarayana, T.3
  • 5
    • 0031004738 scopus 로고    scopus 로고
    • Selected examples of enantioselective MBH: (a) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318.
    • Selected examples of enantioselective MBH: (a) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318.
  • 19
    • 85077742361 scopus 로고
    • For alternative approaches to α-acylvinyl anion equivalents, see: a
    • For alternative approaches to α-acylvinyl anion equivalents, see: (a) Sato, Y.; Takeuchi, S. Synthesis 1983, 734-735.
    • (1983) Synthesis , pp. 734-735
    • Sato, Y.1    Takeuchi, S.2
  • 29
    • 1542375011 scopus 로고    scopus 로고
    • Acyl anion additions: (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314-2315.
    • Acyl anion additions: (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314-2315.
  • 32
    • 15244343088 scopus 로고    scopus 로고
    • Trialkoxysilylalkyne addition
    • (d) Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905-908. Trialkoxysilylalkyne addition:
    • (2005) Org. Lett , vol.7 , pp. 905-908
    • Chan, A.1    Scheidt, K.A.2
  • 38
    • 34547211765 scopus 로고    scopus 로고
    • Attempts at using a single base to catalyze both the rearrangement as well as the addition provided low yields of desired product
    • Attempts at using a single base to catalyze both the rearrangement as well as the addition provided low yields of desired product.
  • 41
    • 4143051292 scopus 로고    scopus 로고
    • For reviews of N-heterocyclic carbenes as catalysts, see: a
    • For reviews of N-heterocyclic carbenes as catalysts, see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
    • (2004) Acc. Chem. Res , vol.37 , pp. 534-541
    • Enders, D.1    Balensiefer, T.2
  • 46
    • 33644511103 scopus 로고    scopus 로고
    • Other NHC-catalyzed cyanation reactions: (a) Fukuda, Y.; Maeda, Y.; Ishii, S.; Kondo, K.; Aoyama, T. Synthesis 2006, 589-590.
    • Other NHC-catalyzed cyanation reactions: (a) Fukuda, Y.; Maeda, Y.; Ishii, S.; Kondo, K.; Aoyama, T. Synthesis 2006, 589-590.
  • 55
    • 8544252475 scopus 로고    scopus 로고
    • See ref 17. For a recent review of the Mukaiyama aldol reaction see: Mukaiyama, T. Angew. Chem., Int. Ed. 2004, 43, 5590.
    • See ref 17. For a recent review of the Mukaiyama aldol reaction see: Mukaiyama, T. Angew. Chem., Int. Ed. 2004, 43, 5590.
  • 60
    • 34547175173 scopus 로고    scopus 로고
    • Solvent, hydrogen atoms (including OH) were removed from ORTEP for clarity. X-ray data for 14: C36H45Cl 5N2O, MW, 698.99, T, 153(2) K, λ, 0.71073 Å, monoclinic space group, P2(1)/c, a, 10.0917(8) Å, b, 15.981(12) Å, c, 23.623(18) Å, β= 95.076(1)°, V, 3794.8(5) Å3, Z, 4, Dc, 1.223 g/cm3, μ, 0.411 mm-1, F(000, 415, crystal size 0.30 × 0.29 × 0.28 mm3, independent reflections 9255 [R(int, 0.0930, reflections collected 35196, refinement method was full-matrix least-squares on F 2, goodness-of-fit on F2 was 0.976, final R indices [I > 2σ(I, R1, 0.0906, wR2, 0.2519, R indices (all data) R1, 0.1274, wR2, 0.2519, largest diff. peak and hole 2.047 and -1.193 e Å-3. See the Supporting Information for additional details
    • -3. See the Supporting Information for additional details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.