Chiral N-substituted allylic amine compounds

Patent metadata

Field	Value
Publication number	US-10179330-B2
Application number	US-201715469654-A
Country	US
Kind code	B2
Filing date	Mar 27, 2017
Priority date	Jun 20, 2016
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. A novel chiral copper-ligand nitrosoarene complex is also set forth.

First claim

The invention claimed is:

1. An isolated chemical compound having the formula [Cu(Ligand)2(ArNO)2]X2, wherein X is selected from a group consisting of halides, triflates, sulfates, acetates, and PF6.

2. The chemical compound of claim 1 wherein the compound is a chiral copper-nitrosoarene complex having two nitrogen donor ligands and two counter ions.

3. The chemical compound of claim 1 wherein the copper atom is bonded to two chiral nitrogen-donor ligands selected from the group comprising BINAM and NOBIN.

4. The chemical compound of claim 1 wherein the copper atom is bonded to a nitrosobenzene.

Assignees

• Univ Louisiana At Lafayette

Inventors

• Srivastava Radhey S
• Murru Siva

Classifications

• B01J31/2217 Primary

  At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C07C227/32

  by stereospecific synthesis · CPC title

• C07C211/48

  N-alkylated amines · CPC title

• C07C209/02 Primary

  by substitution of hydrogen atoms by amino groups · CPC title