7241-20-5Relevant articles and documents
Catalytic Enantioselective α,β,γ-Trioxygenation
Chen, Jason S.,Abeykoon, Gayan A.
, p. 6050 - 6053 (2016/01/09)
Applying a catalytic enantioselective aldehyde α-oxygenation condition to an enal substrate led to the discovery of the first α,β,γ-trifunctionalization cascade of enals. Under optimal conditions, a tryptophan-derived imidazolidinone catalyst in fluorinated aromatic solvents provided α,β,γ-trioxyaldehydes in up to 51% isolated yield (average of 80% yield per oxygenation step) and 85:15 er. Substitution at the δ position was tolerated, but not at the α, β, or γ positions. The reaction proceeded through initial TEMPO incorporation at the γ position, and rapid racemization of this intermediate, reversible conjugate addition of water, followed by TEMPO incorporation at the α position to set all three stereocenters with double dynamic kinetic resolution.
Electroorganic synthesis, 62: Anodic heterocoupling (mixed Kolbe electrolysis) of carbohydrate carboxylic acids with alkanoic acids to C-glycosides
Harenbrock, Michael,Matzeit, Agnes,Schaefer, Hans J.
, p. 55 - 62 (2007/10/03)
2-Deoxy carbohydrate carboxylic acids 1-3 were prepared from glucal 4, acetobromoglucose 5, and D-galactose (7), respectively. The acids 1-3 were electrolyzed with different coacids at controlled current in methanol at platinum electrodes in an undivided
