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Volumn 9, Issue 18, 2007, Pages 3535-3538

Mercury-free preparation and selective reactions of propargyl (and propargylic) grignard reagents

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKYNE; ALLYL COMPOUND; BROMIDE; MAGNESIUM; MERCURY; MORPHINAN DERIVATIVE; N PROPARGYL; N-PROPARGYL; ORGANOMETALLIC COMPOUND; PHOSPHORYLCHOLINE; UNCLASSIFIED DRUG; ZINC;

EID: 34548539681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071397f     Document Type: Article
Times cited : (44)

References (55)
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  • 3
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    • 2nd ed, Elsevier: Amsterdam, The Netherlands
    • (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, The Netherlands, 1988; pp 35-36.
    • (1988) Preparative Acetylenic Chemistry , pp. 35-36
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  • 5
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    • Early examples of the preparation of 2a: (a) Stadler, P. A.; Nechvatal, A.; Frey A. J.; Eschenmoser, A. Helv. Chim. Acta 1957, 40, 1373-1409.
    • Early examples of the preparation of 2a: (a) Stadler, P. A.; Nechvatal, A.; Frey A. J.; Eschenmoser, A. Helv. Chim. Acta 1957, 40, 1373-1409.
  • 9
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    • Hopf, H.; Bohm, I.; Kleinschroth, J. Organic Syntheses; Wiley: New York, 1990; Collect. VII, pp 485490.
    • (e) Hopf, H.; Bohm, I.; Kleinschroth, J. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, pp 485490.
  • 10
    • 0011027169 scopus 로고    scopus 로고
    • Preparation of 2b: (a) Mesnard, D.; Miginiac, L. J. Organomet. Chem. 1990, 397, 127-137.
    • Preparation of 2b: (a) Mesnard, D.; Miginiac, L. J. Organomet. Chem. 1990, 397, 127-137.
  • 14
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    • 1 ≠ H): Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969-1980.
    • 1 ≠ H): Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969-1980.
  • 15
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    • Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 18311835.
    • Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 18311835.
  • 16
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    • Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 15791582.
    • Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 15791582.
  • 33
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    • A similar selectivity for the 2-bromo derivative: Hirama, M.; Fujiwara, K.; Shigematu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120-4122.
    • A similar selectivity for the 2-bromo derivative: Hirama, M.; Fujiwara, K.; Shigematu, K.; Fukazawa, Y. J. Am. Chem. Soc. 1989, 111, 4120-4122.
  • 35
    • 34548534079 scopus 로고    scopus 로고
    • While the authors of ref 13 did not mention the preparation, TMSC≡ CMe has been synthesized by the methods
    • While the authors of ref 13 did not mention the preparation, TMSC≡ CMe has been synthesized by the methods:
  • 37
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    • Wang, J.; Gurevich, Y.; Botoshansky, M.'; Eisen, M. S. J. Am. Chem. Soc. 2006, 128, 9350-9351.
    • (b) Wang, J.; Gurevich, Y.; Botoshansky, M.'; Eisen, M. S. J. Am. Chem. Soc. 2006, 128, 9350-9351.
  • 38
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    • See ref 6
    • (c) See ref 6.
  • 39
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    • Reactions with the propargylic copper reagents: (a) Lam, H. W.; Pattenden, G. Angew. Chem., Int. Ed. 2002, 41, 508-511.
    • Reactions with the propargylic copper reagents: (a) Lam, H. W.; Pattenden, G. Angew. Chem., Int. Ed. 2002, 41, 508-511.
  • 41
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    • Wender, P. A.; Hilinski, M. K.; Soldermann, N.; Mooberry, S. L. Org. Lett. 2006,8, 15071510.
    • (c) Wender, P. A.; Hilinski, M. K.; Soldermann, N.; Mooberry, S. L. Org. Lett. 2006,8, 15071510.
  • 42
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    • See ref 7c
    • (d) See ref 7c.
  • 51
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    • Although (1S)-14 is the direct substrate to give (1R)-16, synthesis of (1S)-14 by the asymmetric hydrolysis of the diacetate by PLE of several lots was unsuccessful in our hand. The hydrolysis with PLE: (a) Wang, Y.-F, Chen, C-S, Girdaukas, G, Sih, C. J. J. Am. Chem. Soc. 1984, 106, 3695-3696
    • Although (1S)-14 is the direct substrate to give (1R)-16, synthesis of (1S)-14 by the asymmetric hydrolysis of the diacetate by PLE of several lots was unsuccessful in our hand. The hydrolysis with PLE: (a) Wang, Y.-F.; Chen, C-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1984, 106, 3695-3696.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.