ChemInform Abstract: Enantioselective Synthesis of Optically Active Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboranes to N-Silylimines.

✍ Scribed by Shinichi Itsuno; Katsuhiro Watanabe; Takeshi Matsumoto; Shizue Kuroda; Ayako Yokoi; Ashraf El-Shehawy

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199945051

✦ Synopsis

Enantioselective Synthesis of Optically Active Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboranes to N-Silylimines.

-A variety of chirally modified allylboron reagents, readily generated from the corresponding chiral bidentate ligands and triallylborane in the presence of Et 3 N in THF, are studied in the allylation of N-silylimines. Additionally, several experiments are made with the recently developed enantioselective allylation reagent allyldiisopinocampheylborane. The most effective allylation reagents are found to be the D-camphor and norephedrine derived compounds (II), (IV), and (V) giving with imine (Ia) the corresponding homoallylic amine (III) in up to 96% enantioselectivity. The methallyl and prenyl analogues of boron compounds (IV) and (V), e.g. reagent (VI), also work well for the enantioselective synthesis of amines (VII). -(ITSUNO, SHINICHI;