155203-78-4Relevant academic research and scientific papers
Regioselective carbohydroxylation of enol ethers by a photocycloaddition- hydrogenation sequence
Bach
, p. 1855 - 1858 (1994)
It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Paterno-Buchi reaction the method enables a regioselective access to 1,2-diols 2 starting from olef
Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity
Hof, Robert P.,Kellogg, Richard M.
, p. 2051 - 2060 (2007/10/03)
Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents. Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200). Also, the solvent and acyl donor employed influences the outcome. On the basis of the results of lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained. Full experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given. Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.
Regioselective Ring Opening of Oxetanes by Hydrogenolysis. - A Convenient Method for the Carbohydroxylation of Enol Ethers
Bach, Thorsten
, p. 1045 - 1054 (2007/10/02)
Hydrogenolysis of the 2-aryl-3-(silyloxy)oxetanes 1, 2, 5, and 9 in the presence of Pd(0) catalysts (Pd/C) yields 1,2-diols as ring-opened products almost quantitatively (82-98percent yield).In combination with the preceding photocycloaddition it facilita
