A new type of catalysis by copper(I) salts in the Barbier-type aldehyde allylation with tin(II) chloride. Short syntheses of (±)-lavandulol and its γ, δ-dihydro derivative

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 3, 1994, Pages 277-278

  Imai, Toshiro ^a   Nishida, Shinya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049087801     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39940000277     Document Type: Article

References (9)

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2. R. J. H. Clark, L. Maresca and P. J. Smith, J. Chem. Soc. A, 1970, 2687.
3. M. Goldstein and G. C. Tok, J. Chem. Soc. A, 1971, 2303.
4. E. J. Corey and T. M. Ecklich, Tetrahedron Lett., 1983, 24, 3163.
5. T. Imai and S. Nishida, Synthesis, 1993, 395.
6. For uncatalysed reactions, see the references cited therein., Another type of catalysis has been proposed recently for palladium(0) that catalyses similar carbonyl allylation with allylic alcohols or their derivatives and tin(II) chloride and the reaction is believed to proceed through π-allylpalladium intermediates: Y. Masuyama, J. P. Takahara and Y. Kurusu, J. Am. Chem. Soc., 1988, 110, 4473.
7. For a recent synthesis and former references, see: D. W. McCullough, M. Bhupathy, E. Piccolino and T. Cohen, Tetrahedron, 1991, 47, 9727.
8. H. Schinz and G. Schappi, Helv. Chim. Acta, 1947, 30, 1483.
9. T. L. Macdonald, B. A. Narayanan and D. E. O’Dell, J. Org. Chem., 1981, 46, 1504.