Asymmetric aza-Friedel–Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

The diastereoselective formation of β-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel–Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and SnCl4 combining TBAI as catalyst in DCM at −50 °C.

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