Trost Allylation (Tsuji-Trost Reaction)

J. Tsuji et al., Tetrahedron Lett. 1965, 4387; B. M. Trost, T. J. Fullerton, J. Am. Chem. Soc. 95, 292 (1973).

Palladium-catalyzed allylation of nucleophiles proceeding in an SN2 or SN2′ fashion depending on the catalyst, nucleophile, and substituents on the substrate:

Scope and limitations under neutral conditions: J. Tsuji et al., J. Org. Chem. 50, 1523 (1985); in biphasic media: C. de Bellefon et al., J. Mol. Catal. A. 145, 121 (1999). Application to the synthesis of polyprenoids: E. Keinan, D. Eren, Pure Appl. Chem. 60, 89 (1988). Review of intramolecular applications: B. M. Trost in Adv. Chem. Ser. 230, entitled “Homogeneous Transition Metal Catalyzed Reactions” (ACS, Washington DC, 1992) pp 463-478. Review: C. G. Frost et al., Tetrahedron: Asymmetry 3, 1089-1122 (1992).