1053223-31-6Relevant articles and documents
Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline
Hesek, Dusan,Lee, Mijoon,Yamaguchi, Takao,Noll, Bruce C.,Mobashery, Shahriar
scheme or table, p. 7349 - 7352 (2009/05/07)
(Chemical Equation Presented) 2-Amino-1,5-anhydro-2-deoxy-D-glucitol, a highly functionalized tetrahydropyran, is a versatile building unit in many natural products. A facile route to this type of synthetic building unit from the corresponding 2-aminopyra
Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinite-oxazoline ligands derived from D-glucosamine
Yonehara, Koji,Hashizume, Tomohiro,Mori, Kenji,Ohe, Kouichi,Uemura, Sakae
, p. 9374 - 9380 (2007/10/03)
Novel 2-alkyl- or 2-aryl-4,5-(4,6-O-benzylidene-3-O-(diphenylphosphino)- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazolines (5a-f) have been prepared from D-glucosamine hydrochloride. They work effectively as chiral ligands and provide a high level of enantiomeric excess in palladium-catalyzed allylic alkylation and amination reactions. The allylic alkylation of 1,3-diphenyl-3- acetoxyprop-1-ene with dimethyl malonate proceeds smoothly in the presence of 0.25 mol % [Pd(η3C3H5)Cl]2 and the chiral ligand 5a having the smallest substituent on oxazoline at 0 °C within 6 h to furnish the highest enantiomeric excess (96% ee). The ligand 5a is also effective for the Pd- catalyzed amination of ethyl 1,3-diphenylprop-2-enyl carbonate, leading to the corresponding allylic amine in 94% ee. The full scope and limitations using ligands 5a-f in the allylic substitution reactions are described.