Enantioselective synthesis of tetrahydroisoquinolines via catalytic intramolecular asymmetric reductive amination?

Organic Chemistry Frontiers Pub Date: 2021-02-19 DOI: 10.1039/D0QO01554G

Abstract

A highly efficient intramolecular asymmetric reductive amination transformation catalyzed by an iridium complex of tBu-ax-Josiphos has been realized via a one-pot N-Boc deprotection/cyclization/asymmetric hydrogenation sequence. This convenient and practical method provides chiral tetrahydroisoquinolines, which are of great importance and common in natural products and biologically active molecules, in moderate to high yields (78–96%) and good to excellent enantioselectivities (80–99% ee).

Graphical abstract: Enantioselective synthesis of tetrahydroisoquinolines via catalytic intramolecular asymmetric reductive amination
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