A convenient synthesis of protected and free homoallylic alcohols: Catalytic use of dibutyltin dichloride in the allylation of aldehydes with allyltributyltin

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 3955-3958

  Whitesell, James K ^a   Apodaca, Richard ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029927159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00719-8     Document Type: Article

References (26)

1. For reviews of allylmetal additions to carbonyl compounds, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. (b) Roush, W.R. In Comprehensive Organic Synthesis, Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1.
3. For reviews of the addition of allylic tin reagents to carbonyl compounds, see: (a) Marshall, J.A. Chem. Rev. 1996, 96, 31.
4. (b) Nishigaichi, Y.; Takuwa, A.; Naruja, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
5. 3: Aspinall, H.C.; Browning, A.F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639.
6. 2: Cozzi, P.G.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Synlett 1994, 857.
7. 3: Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958.
8. allyltributyltin / cationic Rh and Ir complexes: Nuss, J.M.; Rennels, R.A. Chem. Lett. 1993, 197.
9. 4NCl or HMPA): Yano, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1992, 65, 66.
10. For a highly effective catalytic enantioselective allylation based on a titanium/BINOL complex, see: (a) Keck, G.E.; Geraci, L.S. Tetrahedron Lett. 1993, 34, 7827.
11. (b) Costa, A.L.; Piazza, M.G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001.
12. Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
13. Whitesell, J.K.; Apodaca, R. Tetrahedron Lett. Accepted for publication.
14. For related discussions, see references 3e, 5, and: (a) Scholl, M.; Lim, C-K; Fu, G.C. J. Org. Chem. 1995, 60, 6229.
15. (b) Scholl, M.; Fu, G.C. J. Org. Chem. 1994, 59, 7178.
16. For a review of the preparation and reactions of allyldibutyltin chloride, see: Tagliavini, G. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A., Ed.; John Wiley and Sons: Chichester, 1995; Vol. 1, p 98.
17. Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 288, 283.
18. For other examples of exchange reactions between tin alkoxides and silicon or acid halides, see note 6 and: (a) Leigh, D.A.; Martin, R.P.; Smart, J.P.; Truscello, A.M. J. Chem. Soc., Chem. Commun. 1994, 1373.
19. (b) Reginato, G.; Ricci, A.; Roelens, S.; Scapecci, S. J. Org. Chem. 1990, 55, 5132.
20. Gambaro, A.; Peruzzo, V.; Plazzogna, G.; Tagliavini, G. J. Organomet. Chem. 1980, 197, 45.
21. 4F as the fluoride ion source. This reagent caused lower yields compared to KF for some substrates.
22. 2) or elution through a short plug of Florisil® with Skelly B (silyl ethers) afforded the pure alcohol derivatives as colorless oils.
23. 1H NMR spectroscopy of the crude reaction mixture. The exchange reaction in eq 5 may not be favorable under these conditions.
24. (formula presented)
25. The following electrophiles provided no protected product in the case of benzaldehyde: methyl iodide; methanesulfonyl chloride; and t-butyldimethylsilyl chloride. Chloromethyl methyl ether gave complex mixures in the presence and absence of catalyst. The use of trimethylsilyl chloride with cinnamaldehyde and cyclohexanecarboxaldehyde gave product mixtures.
26. 4. Evaporation of solvent (residual water was usually present, but no attempt was made to remove it) followed by chromatography of the residue (5:1 Skelly B / EtOAc) yielded the alcohol products as colorless oils.