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Synfacts 2011(2): 0219-0219  
DOI: 10.1055/s-0030-1259360
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

SPINOL-Derived Phosphoric Acids for Addition of Indoles to Imines

Contributor(s): Benjamin List, Steffen Müller, Ilija Čorić
F. Xu, D. Huang, C. Han, W. Shen, X. Lin*, Y. Wang*
Zhejiang University, Hangzhou and Lanzhou University, P. R. of China
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

The synthesis of a novel class of phosphoric acids derived from 1,1′-spirobiindane-7,7′-diol (SPINOL) has been described. Phosphoric acid 1 was identified as an efficient catalyst for the enantioselective Friedel-Crafts reaction of indoles with imines, delivering comparable results to classic BINOL-derived phosphoric acids (see for example: Q. Kang, Z.-A. Zhao, S.-L. You J. Am. Chem. Soc. 2007, 129, 1484). A variety of aromatic imines 3 proved suitable and products 4 were obtained in high yields and with excellent enantioselectivity. Aliphatic imines present a limitation for the current system (product 5).