Stereoselective preparation of primary (E)-allylic amines by the reaction of tantalum-alkyne complexes with metallo-imines

✍ Scribed by Kazuhiko Takai; Hidetoshi Odaka; Yasutaka Kataoka; Kiitiro Utimoto

• Book ID: 104214413
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 312 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73189-3

✦ Synopsis

Treatment of tantalumdkyne complexes with lithio-imines at 25-50 OC fix several hours in the plwence of Me3Al gives primary Q-allylic amines hadg adjaamt terthy cadmu in good to excellent yields.

Organometallic compounds of group 5 metals have been found to be excellent tools for use in organic syntheses.132 The reaction between unsaturated compounds and reagents possessing carbon-metal bonds is a key step in many stereoselective carbon-carbon bond forming processes. Thex considerations coupled with the importance of nitrogen-containing organic molecules prompted us to study stereoselective synthesis of amines, particularly allylic amines. 3 There exist two approaches for the preparation of allylic amines from acetylenes and imine derivatives.