Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid?

Organic & Biomolecular Chemistry Pub Date: 2018-08-03 DOI: 10.1039/C8OB01863D

Abstract

An asymmetric N-alkylation of indole derivatives via the Reissert-type reaction was realized in the presence of a catalytic amount of chiral phosphoric acid. Various enantioenriched indoles with N-1 substituted by 1,2-dihydroisoquinoline could be obtained under mild conditions in good yields and enantioselectivities at room temperature (up to 98% yield, 94% ee). The current method is compatible with gram-scale reaction and the products can undergo versatile chemical transformations.

Graphical abstract: Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid
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