Albers, Thomas;Biagini, Stefano C. G.;Hibbs, David E.;Hursthouse, Michael B.;Malik, K. M. Abdul;North, Michael;Uriarte, Eugenio;Zagotto, Guiseppe published 《Desymmetrization of meso-anhydrides utilizing (S)-proline derivatives》 in 1996. The article was appeared in 《Synthesis》. They have made some progress in their research.Application of 14166-28-0 The article mentions the following:
Meso-anhydrides derived from norbornanes and norbornenes undergo an asym. ring opening upon treatment with (S)-proline derivatives to give amido acids with moderate to excellent enantiomeric excesses. A cyclopropane derived anhydride was also desymmetrized in this way, while cyclohexyl derived anhydrides gave a 1:1 mix. of diastereomers. The origin of the desymmetrization is explained by a model based on steric interactions in the transition state. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .
In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Application of 14166-28-0 It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem