Synthesis of 2-aminocyclopropyl pyrrolidines from glycoaminonitriles

We have developed an expedient method for the synthesis of 2-aminocyclopropyl pyrrolidines from carbohydrate-derived alpha-aminonitriles involving up to five or six steps, the key step being the titanium-mediated aminocyclopropanation on the aminonitrile moiety, followed by cleavage of the protecting groups. (C) 2009 Elsevier Ltd. All rights reserved.