90921-33-8Relevant articles and documents
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.
Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides
Daniel, Paige E.,Weber, Alexandria E.,Malcolmson, Steven J.
supporting information, p. 3490 - 3493 (2017/07/15)
We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.
Grignard reagents in ionic liquids
Law, Man Chun,Wong, Kwok-Yin,Chan, Tak Hang
, p. 2457 - 2459 (2008/09/16)
Grignard reagents were generated from magnesium and organic iodides in the ionic liquid n-butylpyridinium tetrafluoroborate, [bpy][BF4], and they showed different reactivity from classical Grignard reagents in organic solvents. The Royal Society of Chemistry 2006.