83606-10-4

Upstream product

• 115692-66-5 (S)-(-)-2-(trans-but-2-enyl)-2-methylcyclohexanone 
• 115692-71-2 (S)-2-(3-bromobut-2-enyl)-2-methylcyclohex-1-yl 2,4,6-trimethylbenzoates 
• 115692-70-1 (S)-(2-trans-but-2-enyl)-2-methylcyclohexyl 2,4,6-trimethylbenzoate 
• 115692-67-6 (S)-2-(but-3-ynyl)-2-methylcyclohexanols 
• 1728-38-7 methyl enol ether of 2-methylcyclohexanone 
• 147650-39-3 (1R,6R)-1-(Chloroacetoxy)-6-butylbicyclo<4.1.0>heptane 
• 147583-53-7 (1S,6S)-1-Hydroxyx-6-butylbicyclo<4.1.0>heptane 

Relevant academic research and scientific papers

Chiral 2,2-Disubstituted Cyclohexanones; Annulation via Claisen Rearrangement Products

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.