First chemo- and stereoselective reduction of imines using trichlorosilane activated with N-formylpyrrolidine derivatives

✍ Scribed by Fumiaki Iwasaki; Osamu Onomura; Katsuhiko Mishima; Takefumi Kanematsu; Toshihide Maki; Yoshihiro Matsumura

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 63 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00219-2

✦ Synopsis

Trichlorosilane activated with N-formylpyrrolidine derivatives was found to be an effective reagent for reduction of imines to amines. The reagent showed much higher selectivity toward imino groups than carbonyl groups. The reduction of imines using trichlorosilane activated with optically active N-formylproline derivatives gave enantiomerically enriched amines in moderate optical yields (up to 66% ee).