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Conjugate Reduction of <FONT FACE=Symbol>a,b</FONT>-Unsaturated Carbonyl Compounds. Selective Inhibition of Benzyl Ether Hydrogenolysis by NH4OH/MeOH

A series of <FONT FACE=Symbol>a,b</FONT>-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

conjugate reduction; inhibition of benzyl ether hydrogenolysis; chemoselective reduction of alpha; beta-unsaturated compounds; selective catalytic hydrogenation


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