Electrogenerated cyanomethyl anion in organic synthesis: a simple diastereoselective synthesis of cis-3-alkyl-1-benzyl-4-ethoxycarbonyl-β-lactams"

A ready diastereoselective synthesis of cis-3-alkyl-l-benzyl-4-ethoxycarbonyl-beta-lactams has been developed by galvanostatic electrolysis of MeCN-Et4NPF6 Solutions and subsequent addition of a N-(ethoxycarbonyl)methyl-N-benzyl-2-bromoalkyl-carboxamide. The yields in beta-lactams are very high and the cis isomers have been obtained in a large excess, the cis/trans ratios varying from 87/13 to 93/07