Asymmetric hydrogenation of unprotected indoles using iridium complexes derived from P–OP ligands and (reusable) Brønsted acids

Literature Information

Publication Date 2013-12-19
DOI 10.1039/C3GC42132E
Impact Factor 10.182
Authors

José Luis Núñez-Rico, Héctor Fernández-Pérez


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Abstract

Unprotected indoles have been efficiently converted to enantiomerically enriched indolines (up to 91% ee) by a stepwise process: (reusable) Brønsted acid-mediated CC isomerisation and asymmetric hydrogenation using enantioselective iridium catalysts derived from P–OP ligands. This straightforward combination of (reusable) Brønsted acids, which activate the indole ring for hydrogenation by breaking its aromaticity, and enantiomerically pure [Ir(P–OP)]+ complexes as hydrogenation catalysts affords the resulting indolines with high enantioselectivities.

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