Stereochemistry of the oxidation of oximes to nitrocycloalkanes with peroxytrifluoroacetic acid. Protonation of nitronic acid derivatives in cyclohexane systems
Sodiumethanethiolate in methanol is an efficient reducing agent for gem-bromonitro compounds; treatment of the resultant nitronates with a protic acid or with N-chlorosucccinimide gives high yields of the corresponding nitro or gem-chloronitro compounds, respectively.
Cu−Catalyzed Enantioselective Conjugate Addition of Alkylzincs to Cyclic Nitroalkenes: Catalytic Asymmetric Synthesis of Cyclic α-Substituted Ketones
作者:Courtney A. Luchaco-Cullis、Amir H. Hoveyda
DOI:10.1021/ja020605q
日期:2002.7.1
highly enantioselective (>/=92% ee) catalytic method for conjugate addition of alkylzinc reagents to cyclic nitroalkenes is reported. Reactions are promoted in the presence of 0.5-5 mol % (CuOTf)2.C6H6 and 1-10 mol % of chiral amino acid-based phosphine ligands at 0 degrees C in toluene. The Cu-catalyzed reactions can be effectively carried out with small-, medium-, and large-ring nitroalkenes. Depending