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Merck

Direct catalytic asymmetric reductive amination of simple aromatic ketones.

Organic letters (2013-08-14)
Mingxin Chang, Shaodong Liu, Kexuan Huang, Xumu Zhang
RESUMEN

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.

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Sigma-Aldrich
Phenylhydrazine hydrochloride, ≥99%
Sigma-Aldrich
Phenylhydrazine, 97%
Sigma-Aldrich
Iridium, powder, 99.9% trace metals basis
Sigma-Aldrich
Iridium, foil, thickness 0.25 mm, 99.9% trace metals basis
Sigma-Aldrich
Iridium, evaporation slug, diam. × L 0.6 cm × 1.2 cm, 99.9% trace metals basis