Allylstannylation of alkynes via a radical process: Stereoselective synthesis of di- and tri-substituted vinylstannanes

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8539-8542

  Miura, Katsukiyo ^a   Itoh, Daisuke ^a   Hondo, Takeshi ^a   Saito, Hiroshi ^a   Ito, Hajime ^a   Hosomi, Akira ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTIN COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030592707     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01986-7     Document Type: Article

References (24)

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2. 2. Miura, K.; Matsuda, T.; Hondo, T.; Ito, H.; Hosomi, A. Synlett, 1996, 555-556.
3. 4-catalyzed trans-allylstannylation of certain alkynes. Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513-1514.
4. 3B although the yields were less than 5%. Taniguchi, M.; Nozaki, K.; Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1992, 65, 349-353.
5. 1H NMR spectra of the mixtures.
6. 6. Leusink, A. J.; Budding, H. A.; Marsman, J. W. J. Organomet. Chem. 1967, 9, 285-294.
7. 21), and the fast β-elimination prevents the following allylation with 2e. Stork, G.; Mook, R. Jr. J. Am. Chem. Soc. 1987, 109, 2829-2831.
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11. 9. For the hydrostannylation of propargyl alcohols via a radical process, see (a) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093-5096,
12. (b) Ensley, H. E.; Buescher, R. R.; Lee, K. J. Org. Chem. 1982,47, 404-408.
13. 1H NMR analysis involving NOE experiments. Alvanipour, A.; Eaborn, C.; Walton, D. R. M. J. Organomet. Chem. 1980, 201, 233-247.
14. H1 process. For the 1,5-hydrogen transfer, see Bogen, S.; Malacria, M. J. Am. Chem. Soc. 1996, 118, 3992-3993. (formula presented)
15. 3SnH in the presence of AIBN gave α-and β-stannylacrylates in 58% (E:Z = 1:2) and 29% (E only), respectively. The hydrostannylation of ethyl 2-butynoate has been reported by Leusink et al. See ref. 5.
16. 3CN to determine the geometry, but the reaction gave a 5:4 mixture of E-and Z-isomers of the destannylated products. It turned out that 8h underwent protodestannylation without stereochemical retention, unlike 8f and 10f-g.
17. 14. There is a possibility that the syn adduct is formed by stannyl radical-mediated isomerization of the anti adduct. See ref. 4 and the following report. Leusink, A. J.; Budding, H. A.; Drenth, W. J. Organomet. Chem. 1968, 11, 541-547.
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21. Recent papers: (b) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc., 1996, 118, 2748-2749,
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24. (e) Takeda, T.; Matsunaga, K.; Kabasawa, Y.; Fujiwara, T. Chem. Lett. 1995, 771-772.