126824-96-2Relevant academic research and scientific papers
A Novel Stereoselective Route to β-Lactams: Diastereoselective Synthesis of a Key Intermediate for Carbapenem Antibiotic (+)-PS-5
Miyata, Okiko,Fujiwara, Yoko,Ninomiya, Ichiya,Naito, Takeaki
, p. 2861 - 2862 (2007/10/02)
A combination of stereoselective addition of thiophenol to olefins and subsequent substitution of the corresponding sulfonium group with an O-alkylhydroxamate anion has provided a new practical and stereoselective method for the construction of β-lactams which has been successfully applied to the formal asymmetric synthesis of the carbapenem antibiotic (+)-PS-5 1.
Stereospecific Nucleophilic Addition Reactions to Olefins. Addition of Thiols to α,β-Unsaturated Carboxylic Acid Derivatives
Miyata, Okiko,Shinada, Tetsuro,Ninomiya, Ichiya,Naito, Takeaki,Date, Tadamasa,et al.
, p. 6556 - 6564 (2007/10/02)
Stereospecific nucleophilic addition of thiols to derivatives of α,β-unsaturated carboxylic acids is described.The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source.Erythro and threo adducts are obtained with high diastereoselectivity from E and Z olefins, respectively.This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.
