Sharland, Jack C.; Wei, Bo; Hardee, David J.; Hodges, Timothy R.; Gong, Wei; Voight, Eric A.; Davies, Huw M. L. published their research in Chemical Science in 2021. The article was titled 《Asymmetric synthesis of pharmaceutically relevant 1-aryl-2-heteroaryl- and 1,2-diheteroarylcyclopropane-1-carboxylates》.Formula: C3H3ClO3 The article contains the following contents:
This study described general methods for the enantioselective syntheses of pharmaceutically relevant 1-aryl-2-heteroaryl- and 1,2-diheteroarylcyclopropane-1-carboxylates through dirhodium tetracarboxylate-catalyzed asym. cyclopropanation of vinyl heterocycles with aryldiazoacetates. The reactions were highly diastereoselective and high asym. induction could be achieved using either (R)-pantolactone as a chiral auxiliary or chiral dirhodium tetracarboxylate catalysts. For meta- or para-substituted aryl- or heteroaryldiazoacetates the optimum catalyst was Rh2(R-p-Ph-TPCP)4. In the case of ortho-substituted aryl- or heteroaryldiazoacetates, the optimum catalyst was Rh2(R-TPPTTL)4. For a highly enantioselective reaction with the ortho-substituted substrates, 2-chloropyridine was required as an additive in the presence of either mol. sieves or 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). Under the optimized conditions, the cyclopropanation could be conducted in the presence of a variety of heterocycles, such as pyridines, pyrazines, quinolines, indoles, oxadiazoles, thiophenes and pyrazoles. The results came from multiple reactions, including the reaction of Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Formula: C3H3ClO3)
Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Formula: C3H3ClO3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics