α-Hydroxyallylsilanes as Propionaldehyde Enolate Equivalents and Their Use toward Iterative Aldol Reactions

Johal Ruiz (1) , Akondi Srirama Murthy (1) , Thierry Roisnel (1) , Srivari Chandrasekhar (2) , René Grée (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Division of Natural Products Chemistry

Smooth and efficient reaction conditions have been found for the transformation of protected β-hydroxyacylsilanes into the corresponding aldehydes. This opens a new route to iterative aldol reactions, and it has been used for the synthesis of fragments of several bioactive natural products.

Domaines: Chimie

Johal Ruiz, Akondi Srirama Murthy, Thierry Roisnel, Srivari Chandrasekhar, René Grée. α-Hydroxyallylsilanes as Propionaldehyde Enolate Equivalents and Their Use toward Iterative Aldol Reactions. Journal of Organic Chemistry, 2015, 80 (4), pp.2364-2375. ⟨10.1021/acs.joc.5b00031⟩. ⟨hal-01116172⟩