N-Pyrrolidine-2-ylmethyl)-2-hydroxy-3-aminopinanes as novel organocatalysts for asymmetric conjugate additions of ketones to α-nitroalkenes |
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| Authors: | Dmitry E Siyutkin Alexander S Kucherenko Larisa L Frolova Alexander V Kuchin Sergei G Zlotin |
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| Institution: | 1. N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, Russian Federation;2. Institute of Chemistry Komi SC, Ural Department Russian Academy of Sciences, Pervomayskaya St., Komi Rep. 48, 167610 Syktyvkar, Russian Federation |
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| Abstract: | Novel stereoisomeric natural pinane-derived bifunctional catalysts 3a–d bearing a pyrrolidine unit have been synthesized and examined in the asymmetric conjugate additions of carbonyl compounds to α-nitroalkenes. Six-membered cyclic ketones react with β-nitrostyrene derivatives in the presence of (1R,2R,3R,5R)-2-hydroxy-3-((S)-pyrrolidin-2-ylmethylamino) pinane 3b (10 mol %) with high conversion to afford with diastereoselectivity (dr (syn/anti) up to 97/3), the corresponding Michael adducts with enantiomeric purities of up to 88% ee. |
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