ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Hydrogel supported chiral imidazolidinone for organocatalytic enantioselective reduction of olefins in water

Alessandro Sacchetti, Filippo Rossi, Arianna Rossetti, Roberto Pesa, and Emanuele Mauri

^aDepartment of Chemistry, Materials and Chemical Engineering “Giulio Natta”, Politecnico di Milano, via Mancinelli 7, 20131 Milan, Italy

E-mail: alessandro.sacchetti@polimi.it

Abstract: Chiral products play an important role particularly in the field of medicinal chemistry, where it is known that enantiomers often have very different biological properties and effects. One of the most powerful tool to obtain a product as a single enantiomer is asymmetric catalysis. Recently, organocatalysis, i.e. the use of small organic molecules to catalyze enantioselective transformations, has emerged as a prominent field in asymmetric synthesis. In this work, the use of hydrogels as a support for a chiral imidazolidinone organocatalyst (MacMillan catalyst) and its application in the reduction of activated olefins mediated by the Hantzsch ester is reported for the first time. Results showed a good activity of hydrogels in respect to both yield and enantioselection.

Keywords: hydrogels – organocatalysis – supported catalysts – MacMillan catalyst

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0232

Chemical Papers 70 (4) 436–444 (2016)