Chloramphenicol Base: A New Privileged Chiral Scaffold in Asymmetric Catalysis

Abstract

This Minireview focuses on the synthetic application of a chloramphenicol base (ANP)‐derived catalyst. In the illustrated examples, ANP derivatives have proven to be readily available and highly versatile catalysts in a wide range of asymmetric transformations, showing high proficiency as both chiral ligands (amino alcohol, Schiff base and oxazoline‐containing ligand) and organocatalyst (hydrogen bonding‐based bifunctional catalyst and phase transfer catalyst).

A highly stereoselective and recyclable microgel-supported bifunctional sulfonamide organocatalyst for asymmetric alcoholysis of meso-cyclic anhydrides: a thermo-responsive “organic nanoreactor”

“…Compared with the above-mentioned Cinchona alkaloid-based chiral scaffold, chloramphenicol base ((1 S ,2 S )-2-amino-1-( p -nitrophenyl)propane-1,3-diol ( 1 )) as a chiral waste makes it an ideal chiral scaffold for organocatalyst design. 17 In addition, it is worth noting that chloramphenicol base was chosen as a chiral source due to the low cost and the easy tunability of its structure, providing great feasibility to molecular modification and polymer synthesis. 18…”

“…Compared with the above-mentioned Cinchona alkaloidbased chiral scaffold, chloramphenicol base ((1S,2S)-2-amino-1-(p-nitrophenyl)propane-1,3-diol (1)) as a chiral waste makes it an ideal chiral scaffold for organocatalyst design. 17 In addition, it is worth noting that chloramphenicol base was chosen as a chiral source due to the low cost and the easy tunability of its structure, providing great feasibility to molecular modification and polymer synthesis. 18 In this work, we report the design and synthesis of a highly active and enantioselective MSCBC organocatalyst (MSCBC = microgel-supported chloramphenicol-based bifunctional catalyst) for the enantioselective alcoholysis of mesoanhydrides with high stereocontrol (Scheme 1).…”

Industrial total synthesis of natural medicines

“…This efficient protocol is used in the industrial synthesis of biotin ( 14) at the multi-ton scale. 17 Moreover, the manufacture of the antiobesity drug orlistat (17) is based on an efficient asymmetric hydrogenation. Although the asymmetric hydrogenation of b-keto ester substrates bearing long alkyl chains to form chiral b-hydroxy esters was challenging, an effective dimeric ruthenium catalyst was found to facilitate this type of reaction.…”

New conformationally flexible and recyclable aryl iodine catalysts from an inexpensive chiral source for asymmetric oxidations

“…Based on our previous study, chloramphenicol base (ANP, 2-amino-1-(4-nitro-phenyl)propane-1,3-diol), as a privileged and unique chiral scaffold, has been widely applied in asymmetric transformations. [57][58][59][60] ANP is the crucial synthon in the industrial production of chloramphenicol (CAP), and only (1R,2R)-ANP is valuable for the construction of antibacterial active isomer of chloramphenicol, while (1S,2S)-ANP is left as a chiral waste. Recycling industrial waste is conducive to pharmaceutical synthesis and environmental protection; therefore, (1S,2S)-ANP is an excellent and perfect chiral source.…”