19687-18-4Relevant articles and documents
Synthesis of chiral odoriferous oxy-derivatives of 1,5,5- trimethylcyclohexene
Winska,Wawrzenczyk
, p. 1887 - 1897 (2008/09/18)
Ten racemic and ten enantiomeric pairs of odoriferous compounds, mainly esters, were obtained from isophorone. The starting material, isophorone was reduced to racemic isophorol, which was resolved in pure enantiomers via the lipase catalyzed esterification. The next steps of syntheses, orthoacetic Claisen rearrangement, reduction of esters, esterification of alcohols or their oxidation were carried out with the racemic and enantiomerically enriched (above 98% ee) compounds. The propionates of isophorol (7, 7a, 7b) and 2-(1,5,5-trimethyl-2-cyclohexen-1-yl)ethanol (10, 10a, 10b) possess the most valuable odoriferous properties, useful for cosmetic and food industries.
The claisen rearrangement in synthesis: Acceleration of the johnson orthoester protocol en route to bicyclic lactones
Jones, Graham B.,Huber, Robert S.,Chau, Sotheary
, p. 369 - 380 (2007/10/02)
Catalysis of the Claisen orthoester rearrangement of triethyl orthoacetate and a number of 2-cycloalken-1-ols has been achieved using acidic catalysis and brief microwave thermolysis in DMF. Unlike conventional methods of thermolysis, very high yields of rearranged products are typically obtained in less than ten minutes, and the Claisen products themselves require no further purification. The synthetic utility of the products so obtained is demonstrated in a general synthesis of functionalized bicyclic lactones.
