Stereocontrolled (Me 3 Si) 3 SiH-Mediated Radical and Ionic Hydride Transfer in Synthesis of 2,3,5-Trisubstituted THF

Simon Grélaud , Valérie Desvergnes (1) , Yannick Landais (2)

1 ICOA - Institut de Chimie Organique et Analytique
2 ISM - Institut des Sciences Moléculaires

Trisubstituted tetrahydrofurans were prepared stereoselectively through a two-step process, involving the addition of an acyl radical to a -silyloxy acrylic ester, followed by an acid-catalyzed desilylationketalization sequence and a final oxocarbenium reduction step. High levels of 1,2-and 1,3-stereocontrol were attained using (Me3Si)3SiH as a radical then ionic hydrogen transfer agent.

Domaines: Chimie organique

Simon Grélaud, Valérie Desvergnes, Yannick Landais. Stereocontrolled (Me 3 Si) 3 SiH-Mediated Radical and Ionic Hydride Transfer in Synthesis of 2,3,5-Trisubstituted THF. Organic Letters, 2016, 18 (7), pp.1542-1545. ⟨10.1021/acs.orglett.6b00303⟩. ⟨hal-02374813⟩