76993-59-4

Upstream product

• 40940-58-7 (1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane 
• 27303-99-7 sodium menthoxide 
• 26127-08-2 (1R,2S,5R)-1-(chloromethoxy)-2-isopropyl-5-methylcyclohexane 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 76993-60-7 (4aS,7aS,11aR,11bR)-6-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxymethyl)-dodecahydro-5,7-dioxa-dibenzo[a,c]cycloheptene 

Relevant academic research and scientific papers

Chiral lithiomethyl ethers by DTBB-catalyzed chlorine-lithium exchange

The reaction of equimolecular amounts of enantiomerically pure (+)- or (-)- chloromethyl menthyl ethers 1. or the phenyl derivative (-)-4 and an electrophile [Me3SiCl, Bu'CHO, PhCHO, (CH2)4CO, Et2CO, PhCOMe, Ph2CO, HCONMe2, PhCH=NPh] with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (5 mol %) in THF at 0°C (Method A) leads, after hydrolysis, to the corresponding functionalized chiral ethers 2 and 5. The reaction can be also carried out in a two step process: tandem lithiation at -90°C followed by reaction with the electrophile (H2O, D2O) at the same temperature (Method B). When prochiral electrophiles are used (Bu'CHO, PhCHO. PhCOMe, PhCH=NPh), low asymmetric induction (1:2) is obtained. Springer-Verlag Iberica 1997.