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You-Cai Xiao, Dr. Chao Wang, Yuan Yao, Prof. Dr. Jian Sun and Prof. Dr. Ying-Chun Chen Direct Asymmetric Hydrosilylation of Indoles: Combined Lewis Base and Brønsted Acid Activation Angewandte Chemie International Edition 50

Article first published online: 20 SEP 2011 | DOI: 10.1002/anie.201105341

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Quite a pair: The first organocatalytic direct asymmetric reduction of unprotected 1H-indoles to chiral indolines has been developed. The reaction proceeds through the generation of electrophilic indolenium ions by a Brønsted acid, and then chiral Lewis base (1) mediated enantioselective hydride transfer with HSiCl3. A variety of chiral indolines were obtained with moderate to excellent enantioselectivity. MOM=methoxymethyl.

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