Guanidinium-tagged Organocatalysts for Direct Aldol Reactions
Jabbar Shah and J¨urgen Liebscher
Institute of Chemistry, Humboldt-University Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany Reprint requests to Prof. J. Liebscher. E-mail: liebscher@chemie.hu-berlin.de
Z. Naturforsch.2011,66b,88 – 94; received October 5, 2010
Hexasubstituted guanidinium moieties have been used as ionic liquid tags for organocatalyts for the first time. Such conjugates were obtained in the (S)-proline and (S)-pyrrolidine-2-ylmethyl series by alkylation reactions of pentasubstituted guanidines. The resulting guanidinium-tagged organocat- alysts were applied to asymmetric direct aldol reactions providing high stereoselectivities and yields and good recyclability, and thus performed better than (S)-proline itself.
Key words:Organocatalysis, Ionic Liquids, Guanidinium Salts, Proline, Asymmetric Synthesis, Aldol Reaction