l-proline catalyzed michael additions of thiophenols to α,β-unsaturated compounds, particularly α-enones, in the ionic liquid [bmim]pf6l-proline催化苯硫酚的michael添加α,β-unsaturated化合物,特别是α-enones,离子液体[bmim]pf6.pdfVIP

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l-proline catalyzed michael additions of thiophenols to α,β-unsaturated compounds, particularly α-enones, in the ionic liquid [bmim]pf6l-proline催化苯硫酚的michael添加α,β-unsaturated化合物,特别是α-enones,离子液体[bmim]pf6.pdf

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l-proline catalyzed michael additions of thiophenols to α,β-unsaturated compounds, particularly α-enones, in the ionic liquid [bmim]pf6l-proline催化苯硫酚的michael添加α,β-unsaturated化合物,特别是α-enones,离子液体[bmim]pf6

Molecules 2006, 11, 197-205 molecules ISSN 1420-3049 Full Paper L-Proline Catalyzed Michael Additions of Thiophenols to α,β- Unsaturated Compounds, Particularly α-Enones, in the Ionic Liquid [bmim]PF6 Peter Kotrusz 1 and Štefan Toma 2,* 1 SYNKOLA, s.r.o., SK-842 15 Bratislava, Slovakia. 2 Faculty of Natural Sciences, Comenius University Bratislava, SK-84215 Bratislava, Slovakia. Author to whom correspondence should be addressed; e-mail: toma@fns.uniba.sk Received: 23 November 2005; in revised form: 8 March 2006 / Accepted: 15 March 2006 / Published: 17 March 2006 Abstract: L-Proline catalyzed additions of 13 different thiols to 11 different α-enone Michael acceptors in [bmim] PF6 are reported. Reasonable to high yields of the reaction products were isolated in most cases. Keywords: Thiols, Enones, Michael Addition, Organocatalysis, Ionic Liquids Introduction Addition reactions of thiols to unsaturated ketones have been studied quite frequently, in particular the stereoselective version where chiral metal complexes are often used as catalysts [1,2]. Asymmetric reactions catalyzed by small molecule organic catalysts have become very attractive in recent years [3- 8]. L-Proline, quinine and ephedrine, as well as 2-(S)-phenylaminomethyl-4-(S)-hydroxypyrrolidine and 2-(S)-(diphenylhydroxymethyl)piperidine and its 1-Boc derivatives have all previously been used as the catalysts for additions of thiols to unsaturated ketones, but they gave only moderate e.e. values [9-14]. Ionic liquids have emerged in recent years as “green” solvents for many organic reactions, including transition metal-catalyz