88292-41-5

Upstream product

• 65253-04-5 (-)-8-phenylmenthol 
• 127-17-3 2-oxo-propionic acid 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 

Downstream Products

• 140147-02-0 (2R,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 
• 140147-01-9 (2R,3S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 
• 139944-71-1 (2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 
• 140147-00-8 (2S,3S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 
• 88292-42-6 (1S)-8-phenylmenthyl lactate 
• 88292-42-6 (1R)-8-phenylmenthyl lactate 
• 105229-95-6 (1R)-8-phenylmenthyl (2S)-2-hydroxy-2,6-dimethyl-6-heptenoate 
• 306292-47-7 (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 138291-07-3 (S)-2-Methylsulfanylthiocarboxyoxy-2-phenyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 138291-09-5 8-Phenylmenthyl (S)-2-phenylpropionate 
• 138291-10-8 (-)-8-Phenylmenthyl (R)-2-phenylpropionate 

Relevant academic research and scientific papers

A diastereoselective radical cyclisation approach to pyroglutamates

The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu3SnH at 80°C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmenthyl ester at 20°C.

Asymmetric Reactions of 8-Phenylmenthyl Pyruvate with Allyltrimethylsilane, Silyl Enol Ethers and Ketene Silyl Acetals

By mediation of TiCl4, allylsilane, silyl enol ethers and ketene silyl acetals attacked (-)-phenylmenthyl pyruvate and (-)-phenylmenthyl phenylglyoxylate at their si-faces.The reactions are hypothesised to proceed with rigid cyclic transition states: anti aldol adducts 16 and 17a were favourably obtained from E-ketene silyl acetals 6 and 7 having E-configuration, whereas syn aldol adducts 18b-21b were predominantly obtained from Z-ketene silyl acetal 18 and Z-silyl enol ethers 19-21.