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Sulphonylated diphenylethylenediamines, method for their preparation and use in transfer hydrogenation catalysis

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Title: Sulphonylated diphenylethylenediamines, method for their preparation and use in transfer hydrogenation catalysis.
Abstract: A diamine of formula (I) is described in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X1, X2, Y1, Y2 or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group. The chiral diamine may be used to prepare catalysts suitable for use in transfer hydrogenation reactions. ...


USPTO Applicaton #: #20090326274 - Class: 568309 (USPTO) - 12/31/09 - Class 568 
Organic Compounds -- Part Of The Class 532-570 Series > Azo Compounds Containing Formaldehyde Reaction Product As The Coupling Component >Amino Nitrogen Containing (e.g., Urea, Sulfonamides, Nitrosamines, Oxyamines, Etc., And Salts Thereof) >Ketones >Benzene Ring Containing >Processes

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The Patent Description & Claims data below is from USPTO Patent Application 20090326274, Sulphonylated diphenylethylenediamines, method for their preparation and use in transfer hydrogenation catalysis.

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CROSS-REFERENCE TO RELATED APPLICATIONS

This is a continuation application claiming priority to U.S. patent application Ser. No. 11/719,478, filed Jul. 17, 2007, now published as U.S. Patent Publication 2008/0081930 A1, and entitled “Sulphonylated Diphenylethylenediamines, Method for their Preparation and Use in Transfer Hydrogenation Catalysis.” The parent application, U.S. patent application Ser. No. 11/719,478, is a filing under 35 U.S.C. 371 of International Application No. PCT/GB2005/050190 filed Nov. 1, 2005, entitled “Sulphonylated Diphenylethylenediamines, Method for their Preparation and Use in Transfer Hydrogenation Catalysis,” claiming priority of United Kingdom Patent Application No. 0425320.9 filed Nov. 17, 2004. The above identified applications are incorporated by reference herein in their entirety.

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT

Not Applicable.

REFERENCE TO A MICROFICHE APPENDIX

Not Applicable.

BACKGROUND

This invention relates to diamines and in particular to substituted diphenylethylenediamines and catalysts derived therefrom. Such catalysts are useful for accelerating asymmetric hydrogenation reactions whose products are useful, for example, as chemical intermediates or reagents for use in the production of fine chemicals or pharmaceutical intermediates.

Catalytic asymmetric hydrogenation involves the activation of molecular hydrogen with chiral metal complexes. However, organic molecules can also be applied as the hydrogen donor in the presence of a suitable chiral catalyst in a process known as transfer hydrogenation. A hydrogen donor such as isopropanol or formic acid is conventionally used with catalysts of the type [(sulphonylated diamine)RuCI(arene)] for the reduction of carbonyl groups. This technology provides a powerful complement to catalytic asymmetric hydrogenation. Transfer hydrogenation, in fact, is particularly suitable for the asymmetric reduction of ketones that are difficult substrates for hydrogenation, such as acetylenic ketones and cyclic ketones.

Heretofore the sulphonylated diamine component of the transfer hydrogenation catalysts has been limited to sulphonylated diphenylethylenediamine (Dpen) and cycloalkyl-1,2-diamines such as 1,2-cyclohexane. For example transfer hydrogenation has been applied using [(tosyl-dpen)RuCI(arene)] catalysts to pharmaceutical products such as 10-hydroxy-dihydro-dibenz-[b,f]-azepines (see WO 2004/031155).

The sulphonylated diamine components used heretofore, while useful, are not equally effective across the range of desirable substrates. Thus, there is a need to expand the range of diamines suitable for use in transfer hydrogenation catalysts that provide catalysts of increased activity, selectivity or stability. We have recognised that, by introducing one or more substituting groups into the phenyl rings of diphenylethylenediamines and by variation of the sulphonate properties, the steric and electronic properties of the diamine component may be usefully adapted.

SUMMARY

Accordingly the present invention provides a diamine of formula (I)

in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X1, X2, Y1, Y2 or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group.

The invention further provides a method for preparing a diamine of formula (I) comprising the steps of forming a substituted spiroimidazole from a substituted diketone of formula (II), where X1, X2, Y1, Y2 and Z are as above, reducing the substituted spiroimidazole to form a substituted diamine, optionally resolving the substituted diamine to an enantiomerically enriched form, and sulphonylating the substituted diamine.

The invention also provides a catalyst comprising the reaction product of a diamine of formula (I) and a suitable compound of a catalytically active metal.



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stats Patent Info
Application #
US 20090326274 A1
Publish Date
12/31/2009
Document #
12493043
File Date
06/26/2009
USPTO Class
568309
Other USPTO Classes
564372, 502167
International Class
/
Drawings
0


Alkyl Group
Amine
Amino Group
Catalysis
Catalyst
Diphen
Ethyl
Ethylene
Hydrogen
Hydrogenation
Reaction
Unsaturated


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