Diallylaluminium-N,N-dimethylaminoethanolate, the first stable allyl-alane suitable for additions to aldehydes, ketones and imines

✍ Scribed by Herbert Schumann; Jens Kaufmann; Sebastian Dechert; Hans-Günther Schmalz

• Book ID: 104250990
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 145 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00571-3

✦ Synopsis

The reaction of AlCl 3 with lithium-N,N-dimethylaminoethanolate (3) in a 1:1 ratio yields the corresponding organoaluminium chloride [Cl 2 Al(m-OCH 2 CH 2 NMe 2 )] 2 (1) from which the diallyl derivative [(CH 2 CHCH 2 ) 2 Al(m-OCH 2 CH 2 NMe 2 )] 2 (4) was synthesized by treatment with 2 equiv. of allyl magnesium bromide. The structures of 1 and 4 were deduced from the 1 H, 13 C, 27 Al NMR spectra and confirmed by X-ray structural determination. The allyl aluminium complex 4 was found to be a useful reagent for the transfer of one allyl group to aldehydes, imines and enones. The 1,2-addition products are formed in high yields.