A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols.
[reaction: see text] A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.
Pinacho Crisóstomo
Fernando R
FR
Instituto Universitario de Bioorgánica Antonio González, Universidad de La Laguna, Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Islas Canarias, Spain.
Carrillo
Romen
R
Martín
Tomás
T
García-Tellado
Fernando
F
Martín
Víctor S
VS
D002241:Carbohydrates / Q000737:chemistry*; D006018:Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D002241:Carbohydrates; D006018:Glycols