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Volumn 5, Issue 5, 2003, Pages 653-655

Regioselective reductive coupling of alkynes and aldehydes leading to allylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; ALLYL ALCOHOL; CARBON; CHROMIUM CHLORIDE; NICKEL CHLORIDE; TRIPHENYLPHOSPHINE; WATER;

EID: 0037538818     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0272996     Document Type: Article
Times cited : (75)

References (26)
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    • For representative examples using hydrozirconation, see: (a) Maeta, H.; Hashimoto, T.; Hasegawa, T.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5965. (b) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
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  • 3
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    • The reactivity of the alkenylboron and -aluminum species toward carbonyl compounds is low even when they are converted to the corresponding ate complexes. Thus, the alkenylboron and -aluminum species are usually converted to the corresponding halides with electrophilic sources of halides (iodine or N-bromosuccinimide), and metalated. (a) Brown, H. C.; Bowman, D. H.; Misumi, S. ; Unni, M. K. J. Am. Chem. Soc. 1967, 89, 4531. (b) Zweifel, G.; Whitney, C. C. J. Am. Chem. Soc. 1967, 89, 2753.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 4531
    • Brown, H.C.1    Bowman, D.H.2    Misumi, S.3    Unni, M.K.4
  • 4
    • 33947334412 scopus 로고
    • The reactivity of the alkenylboron and -aluminum species toward carbonyl compounds is low even when they are converted to the corresponding ate complexes. Thus, the alkenylboron and -aluminum species are usually converted to the corresponding halides with electrophilic sources of halides (iodine or N-bromosuccinimide), and metalated. (a) Brown, H. C.; Bowman, D. H.; Misumi, S. ; Unni, M. K. J. Am. Chem. Soc. 1967, 89, 4531. (b) Zweifel, G.; Whitney, C. C. J. Am. Chem. Soc. 1967, 89, 2753.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 2753
    • Zweifel, G.1    Whitney, C.C.2
  • 7
    • 78650170720 scopus 로고
    • Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675. See also: Takai, K.; Sakogawa, K.; Kataoka, Y.; Oshima, K.; Utimoto, K. Org. Synth. 1995, 72, 180.
    • (1990) Synlett , pp. 675
    • Kamiya, N.1    Chikami, Y.2    Ishii, Y.3
  • 9
    • 0000431466 scopus 로고
    • For representative examples, see: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391. Taylor, R. E.; Chen, Y. Org. Lett. 2001, 3, 2221.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2735
    • Rowley, M.1    Tsukamoto, M.2    Kishi, Y.3
  • 10
    • 0028868420 scopus 로고
    • For representative examples, see: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391. Taylor, R. E.; Chen, Y. Org. Lett. 2001, 3, 2221.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10391
    • MacMillan, D.W.C.1    Overman, L.E.2
  • 11
    • 0035850272 scopus 로고    scopus 로고
    • For representative examples, see: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735. MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391. Taylor, R. E.; Chen, Y. Org. Lett. 2001, 3, 2221.
    • (2001) Org. Lett. , vol.3 , pp. 2221
    • Taylor, R.E.1    Chen, Y.2
  • 16
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    • Takai, K.; Toratsu, C. J. Org. Chem. 1998, 63, 6450. See also a review on water-accelerated organic transformations: Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
    • (1998) J. Org. Chem. , vol.63 , pp. 6450
    • Takai, K.1    Toratsu, C.2
  • 17
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    • Takai, K.; Toratsu, C. J. Org. Chem. 1998, 63, 6450. See also a review on water-accelerated organic transformations: Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
    • (2001) Chem. Commun. , pp. 299
    • Ribe, S.1    Wipf, P.2
  • 23
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    • note
    • 3, <5%.
  • 25
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    • Takai, K.; Utimoto, K. J. Synth. Org. Chem., Jpn. 1988, 46, 66. Fürstner, A. Chem. Rev. 1999, 99, 991.
    • (1999) Chem. Rev. , vol.99 , pp. 991
    • Fürstner, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.