syn-Diastereoselective carbonyl allylation by 1- or 3-substituted prop-2-en-1-ols with tin(II) iodide and tetrabutylammonium iodide

Abstract

1-Substituted or 3-substituted prop-2-en-1-ols cause syn-diastereoselective carbonyl allylation with tin(II) iodide and tetrabutylammonium iodide via the formation of 3-substituted prop-2-enylpolyiodotins to produce syn-1,2-disubstituted but-3-en-1-ols.

References

1. For a review, see: Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
2. For reviews of palladium-catalysed carbonyl allylation by allylic alcohols with tin(II) chloride see: Y. Masuyama, J. Synth. Org. Chem. Jpn., 1992, 50, 202; Y. Masuyama, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, 1994, vol. 3, p. 255.
3. For an α-regioselective carbonyl allylation by allylic alcohols see: Y. Kanagawa, Y. Nishiyama and Y. Ishii, J. Org. Chem., 1992, 57, 6988.
4. For a syn-diastereoselective carbonyl allylation by allylic halides with SnI₂ and TBAI, see: Y. Masuyama, M. Kishida and Y. Kurusu, Tetrahedron Lett., 1996, 37, 7103; Y. Masuyama, A. Ito and Y. Kurusu, Chem. Commun., 1998, 315.
5. J. P. Takahara, Y. Masuyama and Y. Kurusu, J. Am. Chem. Soc., 1992, 114, 2577.
6. For anti-diastereoselective carbonyl allylation by (E)-cinnamyltributyltin or (E)-cinnamyltriphenyltin with BF₃·Et₂O in CH₂Cl₂, see: M. Koreeda and Y. Tanaka, Chem. Lett., 1982, 1299.