Stereoselective intermolecular C-H amination reactions.

Chemical communications (Cambridge, England) (2012-07-04)
Hélène Lebel, Carl Trudel, Cédric Spitz
ABSTRACT

A novel chiral N-mesyloxycarbamate to perform rhodium-catalyzed stereoselective C-H amination reactions is reported. Chiral benzylic and propargylic amines are produced in good yields and selectivities using ethyl acetate as solvent. The corresponding free amines are easily obtained by cleavage of the chiral reagent, which could also be recovered.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Sigma-Aldrich
Propargylamine, 98%
Sigma-Aldrich
Pargyline hydrochloride
Sigma-Aldrich
Benzylamine, purified by redistillation, ≥99.5%
Sigma-Aldrich
Benzylamine hydrochloride
Supelco
Benzylamine, for GC derivatization, LiChropur, ≥99.0%
Sigma-Aldrich
Propargylamine hydrochloride, 95%
Sigma-Aldrich
N-Methyl-N-propargylbenzylamine, 97%