13046-76-9Relevant 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.
Acyclic Stereoselection. 32. Synthesis and Characterization of the Diastereomeric (4S)-Pentane-1,2,3,4-tetrols.
Takai, Kazuhiko,Heathcock, Clayton H.
, p. 3247 - 3251 (2007/10/02)
The stereochemistry of the reaction of the lithium enolate of ester 1 and ketene acetal 3 with aldehyde 2 jas been investigated.The diastereomeric (4S)-pentane-1,2,3,4-tetrols and their corresponding tetraacetate esters have been prepared and characterize
