Proprietary Technologies

CSOL Proprietary Technologies

The 1,2 diamine scaffold is found in a large number of natural products with interesting biological activity and in many important pharmaceutical drugs. Their chiral derivatives are also used by the chemical community as control elements in asymmetric synthesis and catalysis. These derivatives therefore represent an attractive target for the synthetic chemist.

The offered process of 1,2-diamination of unactivated alkenes involves the use of catalytic amounts of a palladium (II) salt and a stoichiometric amount of a hypervalent iodine (III) reagent, as well as two external nitrogen sources. The nitrogen sources used (saccharin and sulfonylimides), apart from being commercially available, insert in a regio- and chemoselective manner into the alkene. Reaction performs at room temperature and in short reaction times in a wide range of solvents. Deprotection of the obtained product to the corresponding 1,2-diamine is straightforward. If necessary, simple resolution of the racemate according to known methods might lead to the enantiomerically pure 1,2-diamine derivatives.

The process works outstandingly well for terminal aliphatic alkenes and also proved to be highly tolerant with functional groups born by the olefin starting material, which makes it attractive for the preparation of highly functionalized 1,2-diamines.

Main advantages:

• 1,2-diamine derivatives are highly relevant for the pharmaceutical and chemical industries
• The process uses commercially available reagents
• The reaction is the first one to use intermolecular processes for the 1,2-diamination of alkenes
• Mild reaction conditions
• High tolerance to the presence of functional groups on the susbtrate of the reaction
• Easy removal of the amine protecting groups
• Each amino group can be independently modified in following steps.

References

Muñiz et al. Angew. Chem Int. Ed. 2010; DOI: 10.1002/anie.201003653