906100-58-1Relevant articles and documents
Highly sterically hindered binaphthalene-based monophosphane ligands: Synthesis and application in stereoselective Suzuki-Miyaura reactions
Meskova, Michaela,Putala, Martin
, p. 894 - 902 (2013)
A series of new sterically hindered (R)-(2′-aryl-1,1′- binaphthalene-2-yl)phosphanes with ortho-substituted phenyls as aryl groups were prepared via Negishi monoarylation of enantiopure 2,2′-dibromo-1, 1′-binaphthalene followed by lithiation and quenching with diphenylphosphanyl or dicyclohexylphosphanyl chloride. These ligands were applied to the stereoselective Suzuki-Miyaura coupling for the preparation of substituted biaryls. The enantioselectivity correlated positively when increasing the hindrance of the 2′-aryl group of the ligand. Using the best performing diphenylphosphane ligand with a 2,6-dimethoxyphenyl aryl group, various arylnaphthalenes were prepared in high to excellent yields (68-99%) with low to good ee (12-75% ee), the latter being comparable to the best values reported when using other chiral monophosphane ligands.
α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether
Wagschal, Simon,Guilbaud, Johan,Rabet, Pauline,Farina, Vittorio,Lemaire, Sébastien
, p. 9328 - 9335 (2015/09/28)
The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.
