A mild preparation of vinyliodides from vinylsilanes

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8647-8650

  Stamos, Dean P ^a   Taylor, Andrew G ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALICHONDRIN B; IODINE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; METHODOLOGY;

EID: 0030602206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02000-X     Document Type: Article

References (18)

1. 1. (a) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc., 1992, 114, 3162-3164.
2. (b) Duan, J. J.-W.; Kishi, Y. Tetrahedron Lett. 1993, 34, 7541-7544 and references cited therein.
3. 2. Stamos, D. P.; Kishi, Y. the preceding letter.
4. 3. (a) Chan, T. H.; Lau, P. W. K.; Mychajlowskij, W. Tetrahedron Lett., 1977, 18, 3317-3320.
5. (b) Miller, R. B.; Reichenbach, J. Tetrahedron Lett., 1974, 15, 543-546.
6. (c) Miller, R. B.; McGarvey, G. J. Org. Chem., 1978, 43, 4424-4431.
7. (d) Huynh, C.; Linstrumelle, G. Tetrahedron Lett., 1979, 20, 1073-1076.
8. (e) Miller, R. B.; McGarvey, G. Synth. Comm., 1978, 8, 291-293.
9. (f) Chan, T. H.; Koumaglo, K. Tetrahedron Lett., 1986, 27, 883-886.
10. (g) Tamao, K.; Akita, M.; Maeda, K.; Kumada, M. J. Org. Chem., 1987, 52, 1100-1106.
11. (h) Barluenga, J.; Alvarez-Garcia, L.J.; Gonzaléz, J. M. Tetrahedron Lett., 1995, 36, 2153-2156.
12. (i) Chan, T. H., Fleming, I. Synthesis, 1979, 761-786.
13. 4. The C.11 epimerization observed may be explained by an early intermediate such as i proceeding to either 2 (the path a) or a silyl enol ether ii (path b), which is then protodesilylated in a conjugate fashion to yield a mixture of 2 and its C.11 epimer. Monochlroacetonitrile might act as a quencher of the generated succinate anion via alkylation, thereby changing the profile of a nucleophile(s) affecting these steps. It is worthwhile noting that iii was isolated in 5∼10% yield either with or without monochloroacetonitrile. (formula presented)
14. 5. trans-Aliphatic vinylsilanes (Table 1A) were prepared via platinum catalyzed hydrosilylation of the parent alkyne as described in reference 3c.
15. 6. cis-Aliphatic vinylsilanes (Table 1A) were prepared from the parent alkynylsilanes and were reduced via the method as described by Eisch, J. J.; Damasevitz, G. A. J. Org. Chem., 1976, 41, 2214-2215.
16. 2 followed by treatment with dodecylmagnesium bromide in THF. The resulting alcohols were then protected as described above.
17. 8. All protected primary- and secondary-alcohol cis-vinylsilanes (Tables 1B and 1C) were prepared as described in reference 6 from cis-1-trimethylsilyl-1-propene-3-ol which was prepared from the trimethylsilyl ether of 3-trimethylsilylpropargyl alcohol by hydroboration with dicyclohexyl borane followed by protonolysis with acetic acid.
18. 9. For vinylsilanes that are not soluble in acetonitrile, propionitrile may be used either with or without monochloroacetonitrile without any adverse affects to the reaction (Table 1A, entry 1-t and 1-c, Table 1B, entry 7-t and 7-c).