216099-56-8

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 13266-91-6 (Z)-1-phenylprop-1-en-1-yl acetate 

Downstream Products

• 5650-40-8 (R)-2-hydroxy-1-phenylpropan-1-one 
• 91111-01-2 (R)-1-oxo-1-phenylpropan-2-yl acetate 
• 5650-40-8 (S)-2-hydroxypropiophenone 

Relevant academic research and scientific papers

First lipase catalysed resolution of epoxy enol esters

We report the first enzyme-catalysed kinetic resolution of epoxy enol esters. The lipase-promoted hydrolysis of these compounds provided α-hydroxyketones or α-hydroxyaldehydes (arising from the spontaneous rearrangement of the epoxy enols) and the residual esters with moderate to good enantioselectivity (E up to 100).

Enantioselective synthesis and stereoselective rearrangements of enol ester epoxides

Enol esters can be epoxidized with high enantioselectivities using the fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. A detailed study of enantiomerically enriched enol ester epoxides has revealed that the acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. The competition between the two pathways is highly dependent upon the nature of the acid catalyst. A strong acid favors retention of configuration and a weak acid favors inversion of configuration. Under thermal conditions, these epoxides rearrange highly stereoselectively with inversion of configuration. Either enantiomer of an α-acyloxy ketone can be formed from one enantiomer of an enol ester epoxide by judicious choice of reaction conditions.

Highly enantioselective epoxidation of enol silyl ethers and esters

High enantioselectivities have been obtained for asymmetric epoxidation of enol silyl ethers and esters using a fructose-derived chiral ketone as catalyst and Oxone as oxidant.