Organic Letters 2013-09-06

Direct catalytic asymmetric reductive amination of simple aromatic ketones.

Mingxin Chang, Shaodong Liu, Kexuan Huang, Xumu Zhang

Index: Org. Lett. 15(17) , 4354-7, (2013)

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Abstract

A green method for chiral amine synthesis, the direct catalytic asymmetric reductive amination, was developed. Phenylhydrazide is an ideal nitrogen source for reductive amination. Molecular sieves play dual roles in this reaction. They help to remove H2O to form imine, as well as promote an imine reduction. f-Binaphane minimizes the inhibition effect from amines and helps the coordination of sterically demanding imines to the iridium center, thus leading to a smooth reaction.