Supramolecular Recognition Patterns − A Cause for Preferred Isomers in Phosphanylated 2-Amino-Thiazole

Supramolecular recognition patterns play a key role in the development of new materials but can also be employed as a methodology in the synthesis of amidophosphine ligands. In 2-phosphanylamino-thiazole, dimerization via hydrogen bonding acts as a template to establish the preferred stereochemistry of the second substitution reaction. Seemingly, the energetic advantage due to N−H hydrogen bonding amounting to 40−90 kJ/mol for a dimeric pattern is sufficient for regio- and stereoselective discrimination.