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. 2010 Dec 17;75(24):8677-80.
doi: 10.1021/jo101640z. Epub 2010 Nov 17.

SPINOL-derived phosphoric acids: synthesis and application in enantioselective Friedel-Crafts reaction of indoles with imines

Fangxi Xu  1 , Dan Huang, Chao Han, Wei Shen, Xufeng Lin, Yanguang Wang
Affiliations

SPINOL-derived phosphoric acids: synthesis and application in enantioselective Friedel-Crafts reaction of indoles with imines

Fangxi Xu et al. J Org Chem. .

Abstract

A new class of chiral phosphoric acids with spirobiindane as scaffold were conveniently synthesized from (S)-1,1'-spirobiindane-7,7'-diol ((S)-SPINOL) and employed to catalyze the asymmetric Friedel-Crafts reaction of indoles with imines to afford 3-indolyl methanamines. High yields (68-97%) and excellent enantioselectivities (up to 99% ee) were obtained.

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