Stereoselective synthesis of 2,5-disubstituted tetrahydrofurans by silicon-directed cyclization of vinylsilanes bearing a hydroxy group

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 487-490

  Miura, Katsukiyo ^a   Hondo, Takeshi ^a   Okajima, Shigeo ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030058854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02187-6     Document Type: Article

References (15)

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4. (c) Boivin T. L. B. Tetrahedron 1987, 43, 3309-3362.
5. (a) Larock, R. C.; Leong, W. W. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 4, pp. 307-309.
6. (b) Harding, K. E.; Tiner, T. H. ibid. 1991; Vol. 4, pp. 363-421 and references cited therein.
7. Miura, K; Okajima, S.; Hondo, T.; Hosomi, A. Tetrahedron Lett., 1995, 36, 1483-1486.
8. These substrates are easily available from 4-pentyn-1-ol in 5 steps.
9. 2Si groups. The release of the strain facilitates proton transfer, step (2) shown in Scheme 1, to accelerate the cyclization.
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11. Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964.
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14. For applications of allylsilanes to organic synthesis using the stabilization of β-silyl carbenium ion by σ-π conjugation, see Hosomi, A. Acc. Chem. Res. 1988, 21, 200-206 and references cited therein.
15. Transition states arising from boat-like conformers are strictly inhibited by a 1,3-allylic strain between the hydroxyalkyl and silyl groups.