Lewis acid-catalyzed stereoselective intramolecular trans- vinylsilylation of unactivated alkynes [10]

Journal of the American Chemical Society

Volumn 121, Issue 15, 1999, Pages 3797-3798

  Asao, Naoki ^a   Shimada, Takashi ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE;

CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; LETTER; MOLECULAR INTERACTION; REACTION ANALYSIS; SIALYLATION; STEREOCHEMISTRY;

EID: 0033594446     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990385p     Document Type: Letter

References (38)

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19. n are as follows: Si-Et, 290 ± 25 kJ/ mol; Li-Et, 209 kJ/mol; Zn-Et, 145 kJ/mol; Al-Et, 242 kJ/mol. See: Skinner, H. A. Adv. Organomet. Chem. 1964, 2, 49-114. Aylett, B. J. Organometallic Compounds; The Main Group Elements, Part 2; 1979; Vol. I.
20. n are as follows: Si-Et, 290 ± 25 kJ/ mol; Li-Et, 209 kJ/mol; Zn-Et, 145 kJ/mol; Al-Et, 242 kJ/mol. See: Skinner, H. A. Adv. Organomet. Chem. 1964, 2, 49-114. Aylett, B. J. Organometallic Compounds; The Main Group Elements, Part 2; 1979; Vol. I.
21. Intramolecular carbomercuration of alkynes using allylsilane in the presence of a stoichiometric amount of mercuric chloride was reported. Huang, H.; Forsyth, C. F. J. Org. Chem. 1997, 62, 8595-8599.
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25. (c) Reference 2b.
26. It is well-known that the reactivity of vinylsilanes toward electrophiles is much lower than that of allylsilanes. Accordingly, it was rather surprising for us to discover that the vinylsilylation of 1 proceeded so smoothly in the presence of Lewis acids. See: (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981. (b) Weber, W. P. Silicon Reagents for Organic Chemistry; Springer-Verlag: Berlin, 1983. (c) Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. (N.Y.) 1989, 37, 57-575.
27. It is well-known that the reactivity of vinylsilanes toward electrophiles is much lower than that of allylsilanes. Accordingly, it was rather surprising for us to discover that the vinylsilylation of 1 proceeded so smoothly in the presence of Lewis acids. See: (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981. (b) Weber, W. P. Silicon Reagents for Organic Chemistry; Springer-Verlag: Berlin, 1983. (c) Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. (N.Y.) 1989, 37, 57-575.
28. It is well-known that the reactivity of vinylsilanes toward electrophiles is much lower than that of allylsilanes. Accordingly, it was rather surprising for us to discover that the vinylsilylation of 1 proceeded so smoothly in the presence of Lewis acids. See: (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981. (b) Weber, W. P. Silicon Reagents for Organic Chemistry; Springer-Verlag: Berlin, 1983. (c) Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. (N.Y.) 1989, 37, 57-575.
29. 1H NMR signals due to very trace amounts of impurities were observed in the NMR spectra of 2a; see Supporting Information. It was impossible to identify the structure of these impurities, although we attempted to separate them from 2a by using GC and HPLC.
30. 3 did not catalyze the cyclization of 1a.
31. The stereostructures of products (2c, 2e, 7b, and 7c) other than 2a were determined similarly by NOE experiments. See Supporting Information.
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