The synthesis of S-(+)-2,2-dimethylcyclopropane carboxylic acid: a precursor for cilastatin

Enantioselective hydrolysis of (R)-2, 2-dimethylcyclopropane carboxamide by immobilized cells of an R-amidase-producing bacterium, Delftia tsuruhatensis CCTCC M 205114, on an alginate capsule carrier

“…Thus, the strain might be used as an S -1 producer [30]. Presently, S -1 is mainly chemically prepared via asymmetric synthesis or resolution of racemic substrates such as (R, S -1) or (R, S -2) [1,25,27,28]. However, these methods suffered from certain flaws such as complex reactions, expensive chiral catalysts, harsh reaction conditions, low recovery and high cost.…”

Chiral Drugs and the Associated Asymmetric Synthesis

“…The (S)-(þ)-2,2-dimethylcyclopropane carboxylic acid (þ)-138, a key building block for the synthesis of cilastatin (137), was prepared from 2-methylpropene and chiral iron carbene complex via asymmetric cyclopropanation reaction and exhaustive ozonolysis with up to 92% ee (Wang et al 1998) (Scheme 10.34). (139) is an unnatural antibiotic that possesses an excellent antibacterial profile as well as enhanced chemical and metabolic stability.…”

Enzymatic Resolution of Racemic Ethyl-2,2- Dimethylcyclopropanecarboxylate ToS-(+)-2,2- Dimethylcyclopropanecarboxylic Acid in a Polar Organic Solvent—Water Medium

“…S-(+)-DMcPA can be prepared either by a chemical processes of asymmetric catalysis or by racemate resolution. however, drawbacks such as the need for expensive chiral ligands, difficult reaction conditions and a number of complicated steps have been reported for the chemical processes (19). in the quest for a mild and cost-effective process for the chiral resolution of racemic DMcPA, alternative biocatalytic processes have recently been developed.…”