Journal
ORGANIC LETTERS
Volume 20, Issue 8, Pages 2143-2147Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00312
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- NSFC
- SUSTech
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The incorporation of Bronsted acid, thiourea anion binding, and transition metal catalysis enables an efficient method to synthesize chiral indolines via hydrogenation of indoles. Catalyzed by a rhodium/ZhaoPhos complex, asymmetric hydrogenation of unprotected indoles is performed smoothly with excellent enantioselectivities (up to 99% ee, up to 400 TON). Bronsted acid HCl activates indoles to form iminium ion intermediates. Mechanistic studies support the assumption that anion binding plays a crucial role as a secondary interaction. DFT calculations reveal an outer-sphere mechanism in this chemical transformation.
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