Composition of matter

Patent metadata

Field	Value
Publication number	US-2016304538-A1
Application number	US-201615186823-A
Country	US
Kind code	A1
Filing date	Jun 20, 2016
Priority date	Aug 7, 2012
Publication date	Oct 20, 2016
Grant date	—

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-BINAM nitrosoarene complex is also set forth.

First claim

1 . A chemical compound having the formula [Cu(BINAM) 2 (ArNO) 2 ]OTf 2 .

2 . The chemical compound of claim 1 wherein the compound is a chiral copper-BINAM nitrosoarene complex.

3 . A chemical compound comprising:
a. a copper atom; b. two nitrosoarenes; c. two BINAM ligands; d. two triflates.

4 . The chemical compound of claim 3 wherein the compound is a chiral copper-BINAM-nitrosoarene complex.

5 . The chemical compound of claim 3 wherein the copper-nitroso complex is chiral.

6 . The chemical compound of claim 3 wherein at least one ligand is chiral.

7 . The chemical compound synthesized from the process of combining copper triflate (Cu(OTf) 2 ), and R(+)-BINAM in the presence of toluene.

8 . The chemical compound of claim 7 wherein the process comprises the steps of first creating a mixture of Cu(OTf) 2 , R(+)-BINAM, and toluene, stirring the mixture, and removing the solvent once a desired chemical compound is produced.

Assignees

• Univ Louisiana At Lafayette

Inventors

• Srivastava Radhey S
• Murra Siva

Classifications

• C07F1/08 Primary

  Copper compounds · CPC title

• C07C209/02 Primary

  by substitution of hydrogen atoms by amino groups · CPC title

• C07F1/005

  without C-Metal linkages · CPC title

• C07C227/32

  by stereospecific synthesis · CPC title

• C07C209/68 Primary

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title