Organocatalytic α-amination–allylation-RCM strategy: enantioselective synthesis of cyclic hydrazines

✍ Scribed by Aram Lim; Jung Hoon Choi; Jinsung Tae

• Book ID: 104095496
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 193 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.06.004

✦ Synopsis

A highly enantioselective method for the synthesis of cyclic hydrazines by using organocatalytic a-amination-allylation-RCM strategy is described. Proline-catalyzed a-amination of aldehydes followed by indium-mediated one-pot allylation of the crude a-hydrazino aldehydes produces 1,2-aminoalcohols in high enantio-and diastereoselectivities. The 1,2-aminoalcohols are further converted into cyclic hydrazines by using ring-closing metathesis (RCM) reaction.