Proline Based Chiral Ionic Liquids for Enantioselective Michael Reaction. (20th November 2014)

• Record Type: Journal Article
• Authors: Nobuoka, Kaoru; Kitaoka, Satoshi; Kojima, Tsutomu; Kawano, Yuuki; Hirano, Kazuya; Tange, Masakazu; Obata, Shunsuke; Yamamoto, Yuki; Harran, Thomas; Ishikawa, Yuich
• Other Names: Ishihara Kazuaki Academic Editor.
• Is Part Of: Organic chemistry international. Volume 2014(2014)
• Publication Date: 2014-11-20
• Subjects: Chemistry, Organic -- Periodicals; Chemistry, Organic; Periodicals; 547
• DOI: 10.1155/2014/836126
• Languages: English
• ISSNs: 2090-200X

Abstract

Abstract : Chiral ionic liquids, starting from (S )-proline, have been prepared and evaluated the ability of a chiral catalyst. In Michael reaction of trans - β -nitrostyrene and cyclohexanone, all the reactions were carried out under homogeneous conditions without any solvent except for excess cyclohexanone. The chiral ionic liquid catalyst with the positive charge delocalized bulky pyrrolidinium cation shows excellent yields (up to 92%), diastereoselectivities (syn/anti = 96/4), and enantioselectivities (up to 95% ee) and could be reused at least three times without any loss of its catalytic activity. Such results demonstrated a promising new approach for green and economic chiral synthesis by using the chiral ionic liquids as a chiral catalyst and a chiral medium.