174867-35-7

Upstream product

• 67-56-1 methanol 
• 148705-96-8 (+)-(αR)-α-hydroxycyclohex-1-eneacetonitrile 
• 4845-04-9 1-cyclohexene-1-methanol 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 

Downstream Products

• 174867-39-1 methyl (+)-(αS)-α-hydroxycyclohex-1-eneacetate 
• 183322-95-4 (R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-cyclohex-1-enyl-ethanol 
• 129017-77-2 (R)-1-(cyclohexen-1-yl)-1,2-ethanediol 

Relevant academic research and scientific papers

Synthesis of (R)- and (S)-2-hydroxy-3-enoic acid esters

The synthesis of (R)- and (S)-2-hydroxy-3-enoic acid esters [(R)-1a-d and (S)-1a-c] is described. The (R) enantiomers were prepared by a Pinner synthesis from the corresponding (R)-cyanohydrins [(R)-2a-d], which in turn were obtained by R-oxynitrilase- (E.C. 4.1.2.10)-catalyzed addition of HCN to the α,β-unsaturated aldehydes 3a-d. For the preparation of the (5) enantiomers an inversion of the configuration had to be implemented. A critical evaluation of the two possible sequences: inversion of the configuration of the cyanohydrins followed by solvolysis of the nitrile function, and solvolysis of the cyanohydrins followed by inversion of the configuration of the resulting α-hydroxy esters, came out in favor of the latter pathway.