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Volumn 72, Issue 21, 2007, Pages 8127-8130

Sodium tetramethoxyborate: An efficient catalyst for Michael additions of stabilized carbon nucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; MICHAEL ACCEPTOR REAGENTS; MICHAEL ADDITIONS; SODIUM BOROHYDRIDE;

EID: 35348853140     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701354c     Document Type: Article
Times cited : (20)

References (44)
  • 1
    • 0003148146 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, Chapter 1.1
    • (a) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.1
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Jung, M.E.1
  • 15
    • 5144220014 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see: Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035-1050.
    • (2004) Adv. Synth. Catal , vol.346 , pp. 1035-1050
    • Methot, J.L.1    Roush, W.R.2
  • 24
    • 35348870075 scopus 로고    scopus 로고
    • 6).
    • 6).
  • 25
    • 35348884505 scopus 로고    scopus 로고
    • We also carried out the same reaction using other solvents, but the yields were lower. See Supporting Information
    • We also carried out the same reaction using other solvents, but the yields were lower. See Supporting Information.
  • 26
    • 0344887064 scopus 로고    scopus 로고
    • Although significant differences in absolute values between pKa values measured in DMSO or acetonitile are expected, the relative acidities do not differ greatly. For that discussion and pKa values of organic compounds in DMSO at 25 °C, see: Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463
    • Although significant differences in absolute values between pKa values measured in DMSO or acetonitile are expected, the relative acidities do not differ greatly. For that discussion and pKa values of organic compounds in DMSO at 25 °C, see: Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
  • 27
    • 6344292004 scopus 로고    scopus 로고
    • - in MeOH: (a) Gut, R. Helv. Chim. Acta 1964, 47, 2262-2278.
    • - in MeOH: (a) Gut, R. Helv. Chim. Acta 1964, 47, 2262-2278.
  • 29
    • 35348834433 scopus 로고    scopus 로고
    • 4 is unable to promote the Michael reaction, ruling out the role of sodium cation as Lewis acid.
    • 4 is unable to promote the Michael reaction, ruling out the role of sodium cation as Lewis acid.
  • 30
    • 0000247517 scopus 로고    scopus 로고
    • Sulfones have been described as poor Lewis bases: Carr, R. V.; Paquette, L. A. J. Am. Chem. Soc. 1980, 102, 853-855.
    • Sulfones have been described as poor Lewis bases: Carr, R. V.; Paquette, L. A. J. Am. Chem. Soc. 1980, 102, 853-855.
  • 42
    • 0037178490 scopus 로고    scopus 로고
    • Michael donor 15 was obtained as 9:1 mixture of E:Z diastereomers: Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 67, 5197-5201.
    • Michael donor 15 was obtained as 9:1 mixture of E:Z diastereomers: Fernández-Rivas, C.; Méndez, M.; Nieto-Oberhuber, C.; Echavarren, A. M. J. Org. Chem. 2002, 67, 5197-5201.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.