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

Bi WangJing-Kun GaoShuo SunZhen-Lu ShenYun-Fang YangRen-Xiao LiangYi-Xia Jia
Published in: Organic letters (2024)
An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of N -( o -bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba) 2 /SPINOL-based phosphoramidite as the chiral catalyst and HCO 2 Na 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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