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Volumn 72, Issue 8, 2007, Pages 2851-2856

Alkylation of H-phosphinate esters under basic conditions

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ELECTROCHEMISTRY; IODINE COMPOUNDS; LOW TEMPERATURE OPERATIONS;

EID: 34247228690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062436o     Document Type: Article
Times cited : (34)

References (66)
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    • Base-promoted alkylations of H-phosphinate esters: (a) Baillie, A. C.; Cornell, C. L.; Wright, B. J.; Wright, K. Tetrahedron Lett. 1992, 33, 5133 (NaH).
    • Base-promoted alkylations of H-phosphinate esters: (a) Baillie, A. C.; Cornell, C. L.; Wright, B. J.; Wright, K. Tetrahedron Lett. 1992, 33, 5133 (NaH).
  • 5
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    • Magnin, D. R.; Biller, S. A.; Dickson, J. K., Jr.; Logan, J. V.; Lawrence, R. M.; Chen, Y.; Sulsky, R. B.; Ciosek, C. P., Jr.; Harrity, T. W.; Jolibois, K. G.; Kunselman, L. K.; Rich, L. C.; Slusarchyk, D. A. J. Med. Chem. 1995, 38, 2596 (NaHMDS).
    • (e) Magnin, D. R.; Biller, S. A.; Dickson, J. K., Jr.; Logan, J. V.; Lawrence, R. M.; Chen, Y.; Sulsky, R. B.; Ciosek, C. P., Jr.; Harrity, T. W.; Jolibois, K. G.; Kunselman, L. K.; Rich, L. C.; Slusarchyk, D. A. J. Med. Chem. 1995, 38, 2596 (NaHMDS).
  • 6
    • 0041858056 scopus 로고    scopus 로고
    • Gallagher, M. J.; Ranasinghe, M. G.; Jenkins, I. D. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 115, 255 (i-PrONa).
    • (f) Gallagher, M. J.; Ranasinghe, M. G.; Jenkins, I. D. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 115, 255 (i-PrONa).
  • 16
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    • For some representative examples of the silicon method: a
    • For some representative examples of the silicon method: (a) Boyd, E. A.; Regan, A. C.; James, K. Tetrahedron Lett. 1994, 35, 4223.
    • (1994) Tetrahedron Lett , vol.35 , pp. 4223
    • Boyd, E.A.1    Regan, A.C.2    James, K.3
  • 20
    • 18744396387 scopus 로고    scopus 로고
    • Ribière, P.; Altamirano-Bravo, K.; Antczak, M. I.; Hawkins, J. D.; Montchamp, J.-L. J. Org. Chem. 2005, 70, 4064. See also refs 1c, 1d, and 1h.
    • (e) Ribière, P.; Altamirano-Bravo, K.; Antczak, M. I.; Hawkins, J. D.; Montchamp, J.-L. J. Org. Chem. 2005, 70, 4064. See also refs 1c, 1d, and 1h.
  • 21
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    • Representative examples: (a) Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. J. Med. Chem. 2003, 46, 2641.
    • Representative examples: (a) Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. J. Med. Chem. 2003, 46, 2641.
  • 40
    • 34247246872 scopus 로고    scopus 로고
    • Other workers have used deoxygenation previously see ref 1k
    • Other workers have used deoxygenation previously (see ref 1k).
  • 41
    • 34247179260 scopus 로고    scopus 로고
    • For applications of the Ciba-Geigy reagents, see:(a) Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G.; Jack, J. Phosphorus Sulfur Relat. Elem. 1987, 30, 571.
    • For applications of the "Ciba-Geigy reagents", see:(a) Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G.; Jack, J. Phosphorus Sulfur Relat. Elem. 1987, 30, 571.
  • 46
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    • Bennett, S. N. L.; Hall, R. G. J. Chem. Soc. Perkin Trans. 1 1995, 1145. See also refs 1c and 1d.
    • (f) Bennett, S. N. L.; Hall, R. G. J. Chem. Soc. Perkin Trans. 1 1995, 1145. See also refs 1c and 1d.
  • 47
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    • Cleavage of ketal protecting group to H-phosphinate: see ref 6
    • Cleavage of ketal protecting group to H-phosphinate: see ref 6.
  • 50
    • 34247208299 scopus 로고    scopus 로고
    • The compounds were inactive
    • The compounds were inactive.
  • 51
    • 34247240077 scopus 로고    scopus 로고
    • CH3C(OEt)2P(O)(OEt)CF2H has been prepared in 95% yield using NaH and was used in situ see ref 1c, The synthetic use of this and other difluorophosphinates described herein will be reported separately
    • 2H has been prepared in 95% yield using NaH and was used in situ (see ref 1c). The synthetic use of this and other difluorophosphinates described herein will be reported separately.
  • 52
    • 34247251593 scopus 로고    scopus 로고
    • For examples of epoxide-opening using the silicon method, see refs 1c and 1k
    • For examples of epoxide-opening using the silicon method, see refs 1c and 1k.
  • 53
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    • CGP 36742/SGS742: (a) Chebib, M.; Vandenberg, R. J.; Froestl, W.; Johnston, G. A. R. Eur. J. Pharmacol. 1997, 329, 223.
    • CGP 36742/SGS742: (a) Chebib, M.; Vandenberg, R. J.; Froestl, W.; Johnston, G. A. R. Eur. J. Pharmacol. 1997, 329, 223.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.