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Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization

A technology of isomers and mixtures, applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds

Inactive Publication Date: 2015-09-02
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] However, the disclosures in these documents on isomerization are not in the context of asymmetric hydrogenation

Method used

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  • Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization
  • Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization
  • Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0252] The present invention is further illustrated by the following experiments.

[0253] Analytical method

[0254] 6,10-Dimethylundec-5-en-2-one (DHGA), (R)-6,10-Dimethylundec-2-one (THGA) and (R)-6, GC determination of E / Z-ratio and / or purity of 10,14-trimethylpentadeca-5-en-2-one (R-THFA):

[0255] Agilent 6850, column DB-5HT (30 m, 0.25 mm diameter, 0.10 μm film thickness), 107 kPa helium carrier gas). The sample was injected as a solution in hexane with a split ratio of 300:1, an injector temperature of 200°C, and a detector temperature of 350°C. Oven temperature program: 100°C (8min), 10°C / min to 200°C (1min), 20°C / min to 220°C (4min), running time 24min.

[0256] GC Determination of the Purity of (6R,10R)-6,10,14-Trimethylpentadecan-2-one

[0257] Agilent 6850, column DB-5HT (30 m, 0.25 mm diameter, 0.10 μm film thickness), 115 kPa helium carrier gas). The sample was injected as a solution in hexane with a split ratio of 300:1, an injector temperature of 200°C,...

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Abstract

The present invention relates to a process of manufacturing compound having stereogenic centres from a mixture of E / Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centres. The process involves an asymmetric hydrogenation and an isomerization step. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.

Description

technical field [0001] The present invention relates to the field of asymmetric hydrogenation and synthesis of chiral ketones, aldehydes, acetals and ketals. Background of the invention [0002] Chiral ketones and chiral aldehydes are very important products or intermediates for the synthesis of compounds in the field of flavorings and fragrances or pharmaceuticals and vitamins. [0003] These products possess a stereogenic center that makes their properties very unique. [0004] One possible approach to the formation of stereoisomeric carbon centers is the addition of compounds, especially molecular hydrogen, to the prochiral carbon-carbon double bonds of suitable starting materials. [0005] Classical chemical reactions mainly produce mixtures of stereoisomers at said stereogenic centers and require the use of expensive separation processes. [0006] Therefore, there has long been a great need for highly stereoselective reactions leading to specific stereoisomeric config...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/62C07C45/67C07C49/04C07C47/02
CPCC07B2200/07C07C45/62C07C45/67C07C41/20C07C41/60C07C49/04C07C47/02C07C43/313
Inventor 沃纳·邦拉蒂托马斯·内切尔乔纳森·艾伦·米德洛克雷奈·托拜厄斯·史德姆勒格拉尔杜斯·卡雷尔·玛丽亚·韦尔兹尔安德里亚斯·翰德里克斯·玛丽亚·弗里斯·德
Owner DSM IP ASSETS BV