Expanding cyclitol structural diversity by biocatalysis and metalocatalysis. A click chemistry approach.
The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol, combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO(4) · 5H(2)O as catalyst in toluene-H(2)O at room temperature.
de la Sovera
Victoria
V
Departamento de Química Orgánica, Facultad de Química, UdelaR, Montevideo, Uruguay.
Bellomo
Ana
A
Pena
Jesus M
JM
Gonzalez
David
D
Stefani
Hélio A
HA
D055162:Biocatalysis; D057930:Click Chemistry / Q000379:methods*; D054812:Cyclitols / Q000138:chemical synthesis / Q000737:chemistry*; D049308:Dioxygenases / Q000378:metabolism; D010165:Palladium / Q000737:chemistry*; D016958:Pseudomonas putida / Q000201:enzymology
D054812:Cyclitols; D010165:Palladium; D049308:Dioxygenases