1273587-70-4Relevant academic research and scientific papers
Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst
Momiyama, Norie,Okamoto, Hiroshi,Shimizu, Masahiro,Terada, Masahiro
, p. 464 - 475 (2015)
A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2], prepared from LiTMP (2 equiv) and MgBr2 (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F10BINOL derived chiral mono-phosphoric acid (R)-19 as the chiral Br?nsted acid catalyst. The catalyst (R)-19 performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464-475, 2015.
Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C 1-symmetric NHC-Cu complexes
Vieira, Erika M.,Snapper, Marc L.,Hoveyda, Amir H.
, p. 3332 - 3335 (2011/05/04)
A catalytic method for enantioselective synthesis of homoallylamides through Cu-catalyzed reactions of stable and easily accessible (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkenyl-substituted N-phosphinoylimines is disclosed. Transformations are promoted by 1-5 mol % of readily accessible NHC-Cu complexes, derived from C1-symmetric imidazolinium salts, which can be prepared in multigram quantities in four steps from commercially available materials. Allyl additions deliver the desired products in up to quantitative yield and 98.5:1.5 enantiomeric ratio and are amenable to gram-scale operations. A mechanistic model accounting for the observed selectivity levels and trends is proposed.
