Synthesis of Enantiopure syn-beta-Amino Alcohols. A Simple Case of Chelation-Controlled Additions of Diethylzinc to alpha-(Dibenzylamino) Aldehydes |
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| Authors: | Andrés José M Barrio Roberto Martínez María A Pedrosa Rafael Pérez-Encabo Alfonso |
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| Institution: | Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain. |
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| Abstract: | Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral alpha-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6. |
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