Access to P-stereogenic compounds via desymmetrizing enantioselective bromination

Abstract

A novel and efficient desymmetrizing asymmetric ortho-selective mono-bromination of bisphenol phosphine oxides under chiral squaramide catalysis was reported. Using this asymmetric ortho-bromination strategy, a wide range of chiral bisphenol phosphine...

Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4‐Dihydropyridines by C(sp3)−H Bromination

“…Yeung's group developed a bifunctional amino‐urea catalyzed EDB for obtaining chiral bisphenol [12f] . Li and co‐workers developed an interesting chiral squaramide catalyzed EDB for the preparation of P‐stereogenic compounds [12g] . In contrast, the EDB of the sp 3 C−H bond is unprecedented.…”

Recent advances towards organocatalytic enantioselective desymmetrizing reactions

“…This potent skeleton could be applied to the scalable synthesis of CPAs and phosphoramidite ligands, which may find utilization in asymmetric catalysis. Very recently, Li applied Trends in Chemistry this strategy to the construction of brominated bisphenol phosphine oxides (54) enabled by squaramide catalysis [70].…”

Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine P-Sulfides as a Route to P-Chiral Catalysts

“…Among them, the desymmetrisation of prochiral phosphorus substrates seems particularly interesting. Such transformations were performed mainly in a chemical manner, using chiral catalysts (for some recent results see [3,4]). There are only a few examples of the use of enzymes as catalysts, such as desymmetrisation [5][6][7][8], three of which came from our laboratory [5,7,8] (vide infra).…”