17520-16-0Relevant articles and documents
Chiral 2,2-Disubstituted Cyclohexanones; Annulation via Claisen Rearrangement Products
Grattan, T. J.,Whitehurst, J. S.
, p. 11 - 18 (2007/10/02)
The methyl enol ether of 2-methylcyclohexanone reacts regiospecifically with the optical active forms of but-3-yn-2-ol and but-3-en-2-ol. (R)-But-3-yn-2-ol yields an approximately 4:1 mixture of (R)-2-methyl-2-(R-buta-1,2-dienyl)cyclohexanone and the corresponding SR compound.By contrast the but-3-en-2-ol reaction is ca. 96percent enantioselective; (R)-but-3-en-2-ol gives (R)-2-(trans-but-2-enyl)-2-methylcyclohexanone and (S)-but-3-en-2-ol gives the corresponding (S)-cyclohexanone.These Claisen rearrangement products have been transformed into Robinson-type annulated ketones.Cleavage of some highly hindered esters has been carried out efficiently by sodium methylsulphinyl-methanide in dimethyl sulphoxide.
Absolute Configuration of 1,2-Disubstituted trans-Cyclodecenes Based on Chemical Correlation with (+)-Dimethyl (2R)-2-Butyl-1-methyloctanedioate
Marshall, James A.,Flynn, Katherine E.
, p. 7430 - 7435 (2007/10/02)
The absolute configuration of (-)-trans-1,2-dimethylcyclodecene (4) has been determined to be R through chemical correlation with (+)-dimethyl (2R)-2-butyl-2-methyloctanedioate (13).Diester 13 was prepared from (+)-(4aS)-4a-methyl-2,3,4,4a,5,6,7,8-octahyd
