1114384-60-9Relevant articles and documents
Fast and enantioselective production of 1-aryl-1-propanols through a single pass, continuous flow process
Pericas, Miquel A.,Herrerias, Clara I.,Sola, Lluis
, p. 927 - 932 (2008)
A functional polymer 4, obtained by reaction of (R)-2-(1-piperazinyl)-1,1, 2-triphenylethanol with a Merrifield resin, has been loaded in a packed bed reactor and used as catalyst for the continuous enantioselective production of 1-arylpropanols by ethyla
2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes
Lauzon, Samuel,Ollevier, Thierry
supporting information, p. 11025 - 11028 (2021/11/03)
A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α′-CF3-diol ligand was highlighted in the ZnII-catalyzed asymmetric ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes. Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcohols in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). As observed from single crystal diffraction analysis, the complexation of the 2,2′-bipyridine-α,α′-CF3-diol ligand generates an unusual hexacoordinated ZnII.
Chiral Lithium Amido Zincates for Enantioselective 1,2-Additions: Auto-assembling Reagents Involving a Fully Recyclable Ligand
Rouen, Mathieu,Chaumont, Pauline,Barozzino-Consiglio, Gabriella,Maddaluno, Jacques,Harrison-Marchand, Anne
supporting information, p. 9238 - 9242 (2018/06/04)
A methodology consisting in carrying out enantioselective nucleophilic 1,2-additions (ee values up to 97 %) from cheap, easily accessible, and never described before, chiral lithium amido zincates is presented. These multicomponent reactants auto-assemble when mixing, in a 1:1 ratio, a homoleptic diorganozinc (R2Zn) with a chiral lithium amide (CLA). The latter, obtained after a single reductive amination, plays the role of the chiral inductor and is fully recoverable thanks to a simple acid–base wash, allowing being recycled and re-use without loss of stereochemical information.
