1401797-89-4

Upstream product

• 576-83-0 2,4,6-trimethylphenyl bromide 
• 107-19-7 propargyl alcohol 

Downstream Products

• 1447974-67-5 5-(chloromethyl)-5-mesityloxazolidin-2-one 
• 1448165-24-9 5-(chloromethyl)-5-mesityloxazolidin-2-one 
• 15135-12-3 2-(3-bromoprop-1-en-2-yl)-1,3,5-trimethylbenzene 
• 1447974-81-3 2-mesitylprop-2-en-1-amine 
• 1447974-58-4 tert-butyl (2-mesitylallyl)carbamate 

Relevant academic research and scientific papers

Solvent-dependent enantiodivergence in the chlorocyclization of unsaturated carbamates

A remarkable solvent-controlled enantiodivergence is seen in the hydroquinidine 1,4-phthalazinediyl diether ((DHQD)2PHAL)-catalyzed chlorocyclization of unsaturated carbamates. Eyring plot analyses of this previously unreported reaction are used to probe and compare the R- and S-selective pathways. In the CHCl3/hexanes solvent system, the pro-R process shows a surprising increase in selectivity with increasing temperature. These studies point to a strongly solvent-dependent entropy-enthalpy balance between the pro-R and pro-S pathways. Two solvents, two enantiomers: Enantiodivergent hydroquinidine 1,4-phthalazinediyl diether ((DHQD) 2PHAL)-catalyzed chlorocyclization of unsaturated carbamates, controlled solely by the choice of solvent, yields oxazolidinones in high enantioselectivity (see scheme; DCDMH=1,3-dichloro-5,5-dimethyl hydantoin). The origin of the observed enantiodivergence is traced back to a solvent-selected entropy-enthalpy balance between pro-R and pro-S pathways that dictates the course of the reaction. Copyright