Epoxide ring-opening approach to the synthesis of diverse trisubstituted cyclopentanes

Abstract

The regiospecificity of the epoxide ring-opening reactions of (1RS,2SR,3SR)-1,2-epoxy-3-(N-benzyl-N-methylamino)-cyclopentane 1 and (1RS,2SR,3SR)-1,2-epoxy-3-(N,N-dibenzylamino)-cyclopentane 2 with O- and C-nucleophiles has been explored. It has been shown that electronic and steric factors could affect the regioisomeric ratio of the products due to the possibility for a nucleophile to attack both oxirane carbon atoms. New mimics of 2-deoxystreptamine (2-DOS), the main structural motif of aminoglycoside type antibiotics, have been synthesized.