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Volumn 10, Issue 5, 2008, Pages 861-864

The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes: Synthesis of (E)-1 -tributylstannyl-1 -alkenes

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EID: 51049124099     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702982x     Document Type: Article
Times cited : (70)

References (31)
  • 4
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    • More recent work with Mo catalysts has led to the development of methods to selectively prepare 2-tributylstannyl-1 -alkenes with good regioselectivities and is thus complementary to the method described herein: (a) Kazmaier, U.; Schauss, D.; Pohlman, M. Org. Lett. 1999, 1, 1017-1019.
    • More recent work with Mo catalysts has led to the development of methods to selectively prepare 2-tributylstannyl-1 -alkenes with good regioselectivities and is thus complementary to the method described herein: (a) Kazmaier, U.; Schauss, D.; Pohlman, M. Org. Lett. 1999, 1, 1017-1019.
  • 7
    • 33846246029 scopus 로고    scopus 로고
    • Recent examples: (a) Volgraf, M.; Gorostiza, P.; Szobota, S.; Helix, M. R.; Isacoff, E. Y.; Trauner, D. J. Am. Chem. Soc. 2007, 129, 260-261.
    • Recent examples: (a) Volgraf, M.; Gorostiza, P.; Szobota, S.; Helix, M. R.; Isacoff, E. Y.; Trauner, D. J. Am. Chem. Soc. 2007, 129, 260-261.
  • 10
    • 0031116387 scopus 로고    scopus 로고
    • The effect of different catalysts on the hydrostannation of a propargylglycine derivative has been reported: Crisp, G. T, Gebauer, M. G. J. Organomet. Chem. 1997, 532, 83-88
    • The effect of different catalysts on the hydrostannation of a propargylglycine derivative has been reported: Crisp, G. T.; Gebauer, M. G. J. Organomet. Chem. 1997, 532, 83-88.
  • 17
    • 58149185704 scopus 로고    scopus 로고
    • To test if 4b might arise from protiodestannylation of 2b, 2b was isolated and re-subjected to the reaction conditions (Table 2, entry 3). No 4b was detected.
    • To test if 4b might arise from protiodestannylation of 2b, 2b was isolated and re-subjected to the reaction conditions (Table 2, entry 3). No 4b was detected.
  • 19
    • 0035961019 scopus 로고    scopus 로고
    • 4 salts of trialkylphosphines is preferred to use of the free phosphine: Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
    • 4 salts of trialkylphosphines is preferred to use of the free phosphine: Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
  • 20
    • 58149187097 scopus 로고    scopus 로고
    • 3P (148°): Meijboom, R.; Muller, A. Acta Crystallogr. 2006, E62, m2642-m2644.
    • 3P (148°): Meijboom, R.; Muller, A. Acta Crystallogr. 2006, E62, m2642-m2644.
  • 21
    • 58149177767 scopus 로고    scopus 로고
    • 2 at 0 °C for these hydrostannations.
    • 2 at 0 °C for these hydrostannations.
  • 22
    • 0034917285 scopus 로고    scopus 로고
    • The effect of different oxygen substituents on the regioselectivity of Pd-catalyzed hydrostannations has been documented: Rice, M. B, Whitehead, S. L, Horvath, C. M, Muchnij, J. A, Maleczka, R. E, Jr. Synthesis 2001, 1495-1504
    • The effect of different oxygen substituents on the regioselectivity of Pd-catalyzed hydrostannations has been documented: Rice, M. B.; Whitehead, S. L.; Horvath, C. M.; Muchnij, J. A.; Maleczka, R. E., Jr. Synthesis 2001, 1495-1504.
  • 24
    • 20644449037 scopus 로고    scopus 로고
    • One-pot hydrostannation/Stille couplings have been reported: (a) Maleczka, R. E., Jr.; Terstiege, I. J. Org. Chem. 1998, 63, 9622-9623.
    • One-pot hydrostannation/Stille couplings have been reported: (a) Maleczka, R. E., Jr.; Terstiege, I. J. Org. Chem. 1998, 63, 9622-9623.
  • 30
    • 0002514158 scopus 로고    scopus 로고
    • Other syntheses: (a) Yadav, J. S.; Deshpande, P. K.; Reddy, E. R. Synth. Commun. 1989, 19, 125-134.
    • Other syntheses: (a) Yadav, J. S.; Deshpande, P. K.; Reddy, E. R. Synth. Commun. 1989, 19, 125-134.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.