Ibuprofen, diastereoselectivity

S)-Naproxen, 18, and S-ibuprofen, 19, are important and widely used analgesics with annual sales of about US 1.4 billion and a production volume of about 8000 tons. A technical feasible use of R,R-tartaric acid as chiral auxiliary was demonstrated in the Zambon Process for S-naproxen manufacture [3]. The diastereoselective bromination is followed by bromine hydrogenolysis and hydrolysis to produce S-naproxen in 75 percent overall yield. 

Figure 3.3 Complementary diastereoselectivity in the acylation of ft-cyclodextrin with the acid chloride of Ibuprofen and in the hydrolysis of the corresponding cyclodextrin ester ...

Photodecarboxylation of NSAIDs Inside Cyclodextrin Diastereoselective Photodecarboxylation of 2-Phenylpropionic Acid in Zeolite Medium Photolysis of Ibuprofen and the Methyl Ester of Naproxen 64.5 Conclusion.65-11... 

---