Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles.

Org Lett

College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.

Published: May 2024


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Article Abstract

An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of -(-bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba)/SPINOL-based phosphoramidite as the chiral catalyst and HCONa as the hydride source, a series of enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The reductive Heck reaction of formal tetrasubstituted alkene bearing β-hydrogens is therefore realized by inhibiting β-H elimination.

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http://dx.doi.org/10.1021/acs.orglett.4c00775DOI Listing

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