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Volumn 64, Issue 25, 1999, Pages 9189-9193

Diethylzinc: A chain-transfer agent in intermolecular radical additions. A parallel with triethylborane

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; METHACRYLIC ACID METHYL ESTER; ZINC DERIVATIVE;

EID: 0032784299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912404     Document Type: Article
Times cited : (109)

References (52)
  • 5
    • 0002047232 scopus 로고    scopus 로고
    • 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 1789-1790
    • Miyabe, H.1    Ushiro, C.2    Naito, T.3
  • 6
    • 0032509938 scopus 로고    scopus 로고
    • 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 631-634
    • Miyabe, H.1    Shibata, R.2    Ushiro, C.3    Naito, T.4
  • 7
    • 0032541555 scopus 로고    scopus 로고
    • 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431-11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
    • (1998) Tetrahedron , vol.54 , pp. 11431-11444
    • Miyabe, H.1    Shibata, R.2    Sangawa, M.3    Ushiro, C.4    Naito, T.5
  • 8
    • 33748731177 scopus 로고    scopus 로고
    • 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3659-3660
    • Miyabe, H.1    Yoshioka, N.2    Ueda, M.3    Naito, T.4
  • 9
    • 0033515460 scopus 로고    scopus 로고
    • 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
    • (1999) J. Org. Chem. , vol.64 , pp. 2174-2175
    • Miyabe, H.1    Fujishima, Y.2    Naito, T.3
  • 10
    • 0032894908 scopus 로고    scopus 로고
    • 3SnH see: (a) Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789-1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634. (c) Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431- 11444. (d) Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 3659-3660. (e) Miyabe, H.; Fujishima, Y.; Naito, T. J. Org. Chem. 1999, 64, 2174-2175. (f) Miyabe, H.; Ueda, M.; Yoshioka, N.; Naito, T. Synlett 1999, 465-467.
    • (1999) Synlett , pp. 465-467
    • Miyabe, H.1    Ueda, M.2    Yoshioka, N.3    Naito, T.4
  • 14
    • 0344986813 scopus 로고    scopus 로고
    • note
    • 4c have reported the incorporation of two ethyl groups via, respectively, C-C and C-N bond formation, in the triethylborane-promoted addition of ethyl radical to 3. However, in this case the N-alkylated product resulted from nucleophilic substitution of ethyl iodide (used as coreagent) by 8a.
  • 15
  • 25
    • 0033534413 scopus 로고    scopus 로고
    • and refs cited therein
    • (c) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186-195 and refs cited therein.
    • (1999) J. Org. Chem. , vol.64 , pp. 186-195
    • Jones, P.1    Knochel, P.2
  • 35
    • 0032913898 scopus 로고    scopus 로고
    • B-Alkylcatecholboranes, readily available from the reaction of various olefins and catecholborane, have been used to perform radical additions to α,β-unsaturated ketones and aldehydes. See: Ollivier, C.; Renaud, P. Chem. Eur. J. 1999, 5, 1468-1473.
    • (1999) Chem. Eur. J. , vol.5 , pp. 1468-1473
    • Ollivier, C.1    Renaud, P.2
  • 37
    • 0032537674 scopus 로고    scopus 로고
    • For general reviews on organozinc mediated reactions see: (a) Knochel, P.; Almene Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275-8319. (b) Knochel, P. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds; Wiley- VCH: Weinheim, 1998; Vol. 1, pp 467-503.
    • (1998) Tetrahedron , vol.54 , pp. 8275-8319
    • Knochel, P.1    Almene Perea, J.J.2    Jones, P.3
  • 38
    • 0003779363 scopus 로고    scopus 로고
    • Beller, M., Bolm, C., Eds; Wiley-VCH: Weinheim
    • For general reviews on organozinc mediated reactions see: (a) Knochel, P.; Almene Perea, J. J.; Jones, P. Tetrahedron 1998, 54, 8275- 8319. (b) Knochel, P. In Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 467-503.
    • (1998) Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals , vol.1 , pp. 467-503
    • Knochel, P.1
  • 39
    • 0000080839 scopus 로고
    • For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10775-10776
    • Hanson, M.V.1    Rieke, R.D.2
  • 40
    • 0032572088 scopus 로고    scopus 로고
    • For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5114-5115
    • Charette, A.B.1    Beauchemin, A.2    Marcoux, J.-F.3
  • 41
    • 0032558607 scopus 로고    scopus 로고
    • For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7869-7872
    • Alexakis, A.1    Vastra, J.2    Burton, J.3    Benhaim, C.4    Mangeney, P.5
  • 42
    • 0033531148 scopus 로고    scopus 로고
    • For examples of reactions of organozinc reagents with enones, see: (a) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775-10776. (b) Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115. (c) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872. (d) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 1999, 11-12.
    • (1999) J. Chem. Soc., Chem. Commun. , pp. 11-12
    • Yan, M.1    Yang, L.-W.2    Wong, K.-Y.3    Chan, A.S.C.4
  • 43
    • 33748837412 scopus 로고    scopus 로고
    • 2Zn could promote asymmetric epoxidation of enones and nitro alkenes; see: (a) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann. 1997, 1101-1113. (b) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959-3962.
    • (1997) Liebigs Ann. , pp. 1101-1113
    • Enders, D.1    Zhu, J.2    Kramps, L.3
  • 44
    • 0032573443 scopus 로고    scopus 로고
    • 2Zn could promote asymmetric epoxidation of enones and nitro alkenes; see: (a) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann. 1997, 1101-1113. (b) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959-3962.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3959-3962
    • Enders, D.1    Kramps, L.2    Zhu, J.3
  • 47
    • 0344986809 scopus 로고    scopus 로고
    • 3B behaves as a reducing reagent
    • 3B behaves as a reducing reagent.


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