Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups |
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| Authors: | Nikolay E Shevchenko Alexander S Mitiaev Valentine G Nenajdenko |
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| Institution: | a Department of Chemistry, Moscow State University, Moscow 119899, Russia
b Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Strasse, D-28334, Germany |
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| Abstract: | An aldol-type reaction of cyclic imines and cyclic lactims with carbonyl compounds activated by electron withdrawing trifluoromethyl or trichloromethyl groups proceeded without any catalyst under mild condition. β-Hydroxymethyl substituted cyclic imines or imidates are formed as a result of the reaction. The reduction of the prepared imines leads stereoselectively to the cyclic 1,3-aminoalcohols. Application of methyl trifluoropyruvate in this transformation opens an opportunity for the synthesis of γ-aminoacids derivatives which contain pyrrolidine moiety. |
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| Keywords: | Diastereoselectivity Aldol reaction Reduction Cyclic imines Methyl trifluoropyruvate Azaheterocycles Trihalomethylcarbinols |
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