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Volumn 118, Issue 46, 1996, Pages 11377-11390

General method for preparation of allenic zinc reagents by three-carbon homologation of triorganozincates: Convergent three-component coupling of propargylic substrates, triorganozincates, and electrophilic reagents

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOZINC DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

EID: 0029997133     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962136w     Document Type: Article
Times cited : (65)

References (76)
  • 1
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 865-911.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 865-911
    • Knochel, P.1
  • 34
    • 0000431722 scopus 로고
    • Preliminary communication of this work has appeared: (a) Katsuhira, T.; Harada, T.; Maejima, K.; Osada, A.; Oku, A. J. Org. Chem. 1993, 58, 6166. (b) Harada, T. Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723.
    • (1993) J. Org. Chem. , vol.58 , pp. 6166
    • Katsuhira, T.1    Harada, T.2    Maejima, K.3    Osada, A.4    Oku, A.5
  • 35
    • 0028816860 scopus 로고
    • Preliminary communication of this work has appeared: (a) Katsuhira, T.; Harada, T.; Maejima, K.; Osada, A.; Oku, A. J. Org. Chem. 1993, 58, 6166. (b) Harada, T. Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 723
    • Harada, T.1    Osada, A.2    Oku, A.3
  • 37
    • 0002080420 scopus 로고
    • The Formation and Transformations of Allenic and Acetylenic Carbanions
    • Elsevier: Amsterdam
    • (b) Epsztein, R. The Formation and Transformations of Allenic and Acetylenic Carbanions. In Comprehensive Carbanion Chemistry, Vol. 5b; Elsevier: Amsterdam, 1984.
    • (1984) Comprehensive Carbanion Chemistry , vol.5 B
    • Epsztein, R.1
  • 39
    • 10544219519 scopus 로고
    • Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chime. Fr. 1970, 2171 and 1973, 2549.
    • (1973) Bull. Soc. Chime. Fr. , pp. 2549
  • 47
    • 10544226086 scopus 로고    scopus 로고
    • note
    • The nature of leaving groups in 1 also influences to the acidity of acetylenic proton. Thus, deprotonation of mesylate 1a proceeded even at -60°C judging from 90% yield formation of allene 5a (entry 3). On the other hand, deprotonation of carbamate 1d did not proceed in appreciable rate at the same temperature.
  • 48
    • 10544240685 scopus 로고    scopus 로고
    • note
    • 2Zn (n = 0-2) should also be present in the reaction mixture. Although these organozinc species were neglected in order to simplify the discussion, the same conclusion are deduced by considering these species.
  • 56
    • 0000253689 scopus 로고
    • It was reported that the reaction of allenic allanates with aldehydes gave homopropargylic alcohols regioselectively but with low diastereoselectivity; Zweifel, G.: Hahn, G. J. Org. Chem. 1984, 49, 4565.
    • (1984) J. Org. Chem. , vol.49 , pp. 4565
    • Zweifel, G.1    Hahn, G.2
  • 61
    • 0001579610 scopus 로고
    • Heathcock, C. H., Ed.; Pergamon Press: Oxford
    • (a) Fleming, I. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 563.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 563
    • Fleming, I.1
  • 68
    • 10544256045 scopus 로고    scopus 로고
    • note
    • 2SiH that would be produced initially in the reaction of the silylzincates with the terminal alkyne.
  • 71
    • 10544245525 scopus 로고    scopus 로고
    • note
    • The byproduct formation of isomeric allenic alcohols was observed in the reaction of silylzinc reagents 30a and 29a: the reactions with 2-methylpropanal and 6,6-dimethoxyhexanal gave 7-methyl-1-phenyl-5-(dimethylphenylsilyl)-3,4-octadien-6-ol (47a) (14%) and 11,11-dimethoxy-1-phenyl-5-(dimethylphenylsilyl)-3,4-undecadien-6-ol (47b) (11%), respectively.
  • 72
    • 10544250561 scopus 로고    scopus 로고
    • note
    • 2H]-42a (58%-d) were obtained in 77% and 7.8% yield, respectively.
  • 73
    • 10544221969 scopus 로고    scopus 로고
    • note
    • 2BuZnLi. The difference in reactivity might be derived from the differences of ligands.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.