Solid phase synthesis of allylic alcohols via the Baylis-Hillman reaction

Hartmut Richter, Günther Jung
Institut für Organische Chemie, Eberhard-Karls-Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany.

Abstract
An efficient method for the solid phase synthesis of allylic alcohols via the Baylis-Hillman reaction has been developed. In the presence of DABCO® or 3-quinuclidinol the coupling of resin bound acrylic acid with different aldehydes yields allylic alcohols. Aldehydes with different reactivity were used and gave modest to excellent yields upon simply varying the base or the reaction time. The allylic alcohols were reacted with primary amines to form 1,3-aminoalcohols.

Keywords
Baylis-Hillman reaction, combinatorial chemistry, solid-phase synthesis