130562-83-3

Upstream product

• 186581-53-3 diazomethane 
• 107-08-4 1-iodo-propane 
• 139590-65-1 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen fluoromalonate 
• 139590-64-0 methyl (1R,3R,4S)-8-phenyl-p-menthan-3-yl fluoromalonate 
• 139590-66-2 methyl (1R,3R,4S)-8-phenyl-p-menthan-3-yl allyl(fluoro)malonate 
• 130562-75-3 methyl (1R,3R,4S)-8-phenyl-p-menthan-3-yl propylmalonate 

Relevant academic research and scientific papers

Enantioselective Construction of Quarternary Stereogenic Centres Possessing a Fluorine Atom

Fluorination of methyl (1R,3R,4S)-8-phenylmenthyl methylmalonates 2 using lithium hexamethyldisilazide and 1-fluoro-2,4,6-trimethylpyridinium triflate (trifluoromethanesulfonate) gave the (R)-3 and (S)-4 isomers in a 3.8:1 ratio, while fluorination of ethyl-, propyl- and benzyl-malonates 10, 11 and 12 provided the (R)-13, 15 and 17 and (S)-14, 16 and 18 isomers in a 1:1.6-2.0 ratio.On the other hand, alkylation of (1R,3R,4S)-8-phenylmenthyl hydrogen fluoromalonates 26 in the presence of lithium hexamethyldisilazide, followed by esterification with diazomethane, produced the (R)-3, 13, 15, 17 and 27 and (S)-4, 14, 16, 18 and 28 isomers in a 1:5.7-35 ratio.

Enantioselective Synthesis of Monofluorinated Chiral Building Blocks from Malonic Acid

A general method for the preparation of monofluorinated chiral building blocks has been developed by fluorination of methyl phenylmenthyl monoalkylmalonates using lithium hexamethyldisilazide and 1-fluoro-2,4,6-trimethylpyridinium triflate.