188023-68-9

Upstream product

• 218438-83-6 ((2R,3S)-3-Pent-4-enyl-2-trimethylsilanyl-oxiranyl)-methanol 
• 65939-59-5 hept-1-en-6-yne 
• 188023-64-5 Methanesulfonic acid (2R,3S)-3-pent-4-enyl-2-trimethylsilanyl-oxiranylmethyl ester 
• 100-51-6 benzyl alcohol 
• 188023-62-3 (Z)-2-Trimethylsilanyl-octa-2,7-dien-1-ol 

Downstream Products

• 146329-67-1 (R)-3-Hydroxy-2-octanone 

Relevant academic research and scientific papers

Generation and trapping of allene oxides: An approach to chiral, nonracemic α-alkoxyketones

Epoxy mesylates 5 react with a variety of sodium alkoxides to produce the corresponding α-alkoxyketones in good yields. Evidence is presented for the involvement of transient allene oxides in these reactions. Enantiomerically enriched epoxy mesylates (2R,3S)-5a-c were prepared using the Sharpless asymmetric epoxidation reaction as the key step. These precursors rearrange to α-alkoxyketones without significant racemisation under modified reaction conditions (ROK, 18-crown-6, THF, -78°C). The reactions are shown to proceed with stereochemical inversion at the epoxide centre.

Synthesis of chiral α-Alkoxyketones via allene oxides

Treatment of enantiemerically enriched epoxy mesylates 7-9 with potassium alkoxides under carefully controlled reaction conditions (18-crown-6, THF, -78°C) provide the coresponding α-alkoxyketones 10-13 without significant racemisation. The reactions are shown to proceed with net stereochemicaI inversion at the epoxide centre.