Heterocycles

Diastereoselective nucleophilic cyclopropanation of 1, 2-diketones and α-ketoimines with bis (iodozincio) methane

K Nomura, K Asano, T Kurahashi, S Matsubara

Index: Nomura, Kenichi; Asano, Keisuke; Kurahashi, Takuya; Matsubara, Seijiro Heterocycles, 2008 , vol. 76, # 2 p. 1381 - 1399

Full Text: HTML

Citation Number: 9

Abstract

Abstract–A reaction of 1, 2-diketones and α-ketoimines with bis (iodozincio) methane gave cyclopropan-1, 2-diol and 2-aminocyclopropanol respectively via nucleophilic [2+ 1] cycloaddition. The reaction proceeded via a sequential nucleophilic attack of the dizinc reagent to vicinal two carbonyl group. The reaction showed high diastereoselectivity to give cis-isomer via a face-to-face coordination between the substrate and bis (iodozincio) ...