N-Heterocyclic carbene mediated organocatalytic transfer of tin onto aldehydes: An easy access to syn-diols and mechanistic studies

Romain Blanc (1) , Paola Nava (2) , Michel Rajzman (1) , Laurent Commeiras (1) , Jean-Luc Parrain (1)

1 STeRéO
2 CTOM - Chimie Theorique et Modèles

An update of our preliminary communication concerning an efficient organocatalytic procedure for the transfer of tin onto aldehydes was proposed. This update combines 1- a full study of the preparation of γ-silyloxyallylstannanes from β-substituted enals; 2- a "one-pot" sequence (in inter- and intramolecular version) including NHC-catalyzed silylstannation reaction / Lewis Acid promoted allylstannation reaction to furnish the corresponding syn-diols; 3- mechanistic studies of the organocatalytic 1,2-addition

Mots clés: Allylstannation; syn-1; 2-diols; N-heterocyclic carbenes; oragnocatalysis; gamma-silyloxyallylstannanes

Domaines: Chimie organique

Romain Blanc, Paola Nava, Michel Rajzman, Laurent Commeiras, Jean-Luc Parrain. N-Heterocyclic carbene mediated organocatalytic transfer of tin onto aldehydes: An easy access to syn-diols and mechanistic studies. Advanced Synthesis and Catalysis, 2012, 354, pp.2049-2056. ⟨10.1002/adsc.201200063⟩. ⟨hal-00736643⟩