New active-iron based reducing system for carbonyl compounds and imines. Stereoselective reduction of cyclic ketones

Y. MOGLIE; F. ALONSO; C. VITALE; M. YUS; G. RADIVOY

TETRAHEDRON

Elsevier

Año: 2006 vol. 62 p. 2812 - 2819

0040-4020

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 a,b-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.