In 2006,Balskus, Emily P.; Jacobsen, Eric N. published 《α,β-Unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor》.Journal of the American Chemical Society published the findings.Name: 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:
Chiral (salen)Al μ-oxo dimer catalyzes the highly enantioselective conjugate addition of carbon-centered nucleophiles to α,β-unsaturated silyl imides. Allyldimethylsilane-substituted imide I was identified as an optimal substrate, undergoing addition reactions with a variety of nitrile nucleophiles in high yield and enantiomeric excess. The silicon-containing products are synthetically useful chiral building blocks, as demonstrated by their application to an enantioselective total synthesis of the potent proteasome inhibitor (+)-lactacystin. Elaboration of lactam II to the natural product was effected in 12 steps and in 11% overall yield and proceeded through an unusual spiro β-lactone intermediate. This compound was found to inhibit the chymotrypsin-like site of the 26S proteasome at similar levels to known inhibitor clasto-lactacystin β-lactone (omuralide). In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Name: 2-(3-Bromophenyl)acetonitrile)
2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Name: 2-(3-Bromophenyl)acetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts