New active-iron based reducing system for carbonyl compounds and imines. Stereoselective reduction of cyclic ketones |
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| Authors: | Yanina Moglie Cristian Vitale Gabriel Radivoy |
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| Institution: | a Departamento de Química, Instituto de Investigaciones en Química Orgánica (INIQO), Universidad Nacional del Sur Avenida Alem 1253, 8000 Bahía Blanca, Argentina
b Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain |
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| Abstract: | The reaction of different carbonyl compounds and imines with a mixture of iron(II) chloride tetrahydrate, an excess of lithium powder, and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding alcohols and amines, respectively. The process was also applied to the transformation of α,β-unsaturated carbonyl compounds into the corresponding saturated alcohols. The new reducing system exhibited good to excellent diastereoselectivity toward the reduction of different monocyclic and polycyclic ketones. |
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| Keywords: | Reduction Ketones Aldehydes Imines Stereoselectivity Arene catalysis Active iron |
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