183997-42-4

Upstream product

• 108-94-1 cyclohexanone 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 
• 65253-04-5 (-)-8-phenylmenthol 

Downstream Products

• 129017-77-2 (R)-1-(cyclohexen-1-yl)-1,2-ethanediol 
• 203253-78-5 (-)-8-Phenylmenthyl α-(cyclohex-1-enyl)-α-hydroxyacetate 

Relevant academic research and scientific papers

Asymmetric induction in Darzens condensation by means of (-)-8-phenylmenthyl and (-)-menthyl auxiliaries

Asymmetric Darzens condensation of benzaldehyde and various ketones has been investigated. The condensation of acetophenone, propiophenone and symmetric ketones with (-)-8-phenylmenthyl halogenoacetates 3a,b afforded the corresponding glycidic esters cis-12, cis-13 and 15-19 in 77-96% de, respectively, as the major products. Aza-Darzens condensation between N-benzylideneaniline and 3a occurred to give the trans-aziridine 21 as the major isomer in >85% de. The stereochemistry of the major diastereoisomers of cis-12 and 18 was confirmed by their conversion into the known optically active diols 22 and 24. The configuration of the major product of cis-12 was determined to be 2R,3R and that of 18 to be 2R. The geometric and disastereofacial selectivities were understandable in terms of the open-chain or non-chelated antiperiplanar transition state model in the initial aldol-type reaction.

Asymmetric Darzens condensation of ketones with α-chloroacetates by means of (-)-8-phenylmenthyl auxiliary

The Darzens condensation of symmetric and unsymmetric ketones with (-)-8-phenylmenthyl α-chloroacetate diastereoselectively affords glycidic esters in 77-94% de; the stereochemistry [(2R,3R) configuration] of the product is understandable in terms of π-π interaction in the open transition state model.