C2-symmetric diphosphinite ligands derived from carbohydrates. The strong influence of remote stereocenters on asymmetric rhodium-catalyzed hydrogenation.
Modular ligands of C(2) symmetry (13a-e, 14a,b,d, and ent-9), systematically modified at positions 2 and 5, were easily prepared from d-glucosamine, D-glucitol, and tartaric acid, respectively. The application of these ligands in the rhodium-catalyzed hydrogenation of methyl acetamidoacrylate, methyl acetamidocinnamate, and dimethyl itaconate shows that both the configuration and the substituents at positions 2 and 5 of the tetrahydrofuran backbone have a strong influence on the enantioselectivty of the processes.
Aghmiz
Mohamed
M
Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, Pl. Imperial Tarraco 1, 43005 Tarragona, Spain.
Aghmiz
Ali
A
Díaz
Yolanda
Y
Masdeu-Bultó
Anna
A
Claver
Carmen
C
Castillón
Sergio
S
D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D005944:Glucosamine / Q000737:chemistry; D006865:Hydrogenation; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017905:Phosphites / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry*; D013012:Sorbitol / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002241:Carbohydrates; D008024:Ligands; D009942:Organometallic Compounds; D017905:Phosphites; D013012:Sorbitol; D012238:Rhodium; D005944:Glucosamine