Arran manufactures specialised chiral diamines, chiral aminoalcohols and chiral diols, which are used as resolving agents or intermediates in pharmaceutical synthesis. Manufacturing technology includes sophisticated methods of resolution, asymmetric synthesis (using chiral catalysts and auxiliaries) and a combination of these approaches. Arran normally offers both enantiomers of a pair, e.g. (R,R)-(+)-1,2-Diphenylethylenediamine and (S,S)-(-)-1,2-Diphenylethylenediamine, and we can help also with advice on analytical methods and possibly on recycling and other aspects. Chiral Products are listed by chemical name, CAS No. and sign of rotation.

Besides those products offered at normal commercial scale, we have an extensive list of Chiral Products in Development, which can normally be offered from gram scale to multi-kilo scale. Our kilo lab, pilot plant and production facilities are located on one compact site, and this facilitates rapid scale up transfer of technology. With an active development programme, we add new chiral synthons at regular intervals, for applications in asymmetric synthesis and as "building blocks" or intermediates in pharmaceutical chemistry. (Recently, we have introduced the diphenylethanediols (RR) and (SS), and the diphenylprolinols (R) and (S), which are useful precursors for organocatalysts.)

Arising from our work in developing and manufacturing chiral amines (especially diamines) and other chiral substances, we have gained considerable experience over the years in manufacturing coordinating ligands or catalysts based on these, including, for example, those where a transition metal is complexed to a coordinating chiral ligand and these chiral catalysts or auxillaries can be used in the asymmetric synthesis of more complicated molecules, such as pharmaceutical, agrochemical and flavour and fragrance applications. Typical structures, which can be derived from our "building blocks", are shown below:

For a detailed listing see our Chiral Products range and our range of Chiral Products in Development.

Numerous "salen" and other polydentate ligands have been developed and applied in the asymmetric synthesis of pharmaceutical substances worldwide. Arran has worked with many companies on scale up and manufacture of these ligands and catalysts, and in their application in asymmetric synthesis, which is often the next step in the chemical process. Being an independent company, and not part of any large group, we can work on a confidential basis with any customer in this field, and can, of course, also offer the basic building blocks, including for example, from our lists, (R,R) and (S,S)-1,2-trans-Diaminocyclohexanes and substituted derivatives, and also (R,R) and (S,S)-1,2-Diphenylethylenediamine and substituted derivatives. Some interesting literature references are appended, which show possible applications for our "building blocks". We advise normal care and diligence in working on applications which may be the subject of patents or licences.

DPEN Derivatives

Chiral Guanidine

Asymmetric silylation of secondary alcohols
Isobe, Chem. Commun. 2001, 243

Asymmetric Michael addition of glycine imines to
acrylates Isobe, Chem. Commun. 2001, 243

Chiral Phosphoramide

Asymmetric aldol reaction of enol silyl ethers with aldehydes

Denmark, J. Am. Chem. Soc. 1996, 118, 7404
Denmark, J. Org. Chem. 1998, 63, 918

Grubbs Chiral Ruthenium Catalyst

Chem. Eng. News 2002, December 23, 29

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