Enantioselective synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel–Crafts reaction?

Chemical Communications Pub Date: 2019-06-25 DOI: 10.1039/C9CC04057A

Abstract

A highly enantioselective aza-Friedel–Crafts reaction of structurally new ketimines with indoles and pyrrole is developed by using a chiral phosphoric acid as the catalyst. This protocol enables the first enantioselective synthesis of isoquinoline-1,3(2H,4H)-dione derivatives in good to excellent yields (up to 99% yield) and excellent enantioselectivities (up to >99% ee).

Graphical abstract: Enantioselective synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel–Crafts reaction
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