Conjugate reduction of α,β-unsaturated carbonyl compounds. Selective inhibition of benzyl ether hydrogenolysis by NH4OH/MeOH

Abstract

A series of α,β-unsaturated alkyl and aryl ketones, esters and N-methoxy-N-methyl-amides (Weinreb amides) containing an O-benzyl protecting group undergo conjugate reduction by H2/Pd/C in the presence of 2N NH4OH/MeOH at room temperature and ordinary pressure leaving the benzyl group intact. © 1998 Soc. Bras. Química.